Month: October 2022

On September 15, 2005, Constan, Alexander A.; Keshary, Prakash; Maclean, David B.; Paralkar, Vishwas M.; Roman, Doina; Thompson, David D.; Wright, Timothy M. published a patent.Electric Literature of 142327-44-4 The title of the patent was Preparation of heterocyclic compounds as EP2 selective receptor agonists for treating pulmonary hypertension and other conditions. And the patent contained the following:

The present invention relates to methods of treating pulmonary hypertension, facilitating joint fusion, facilitating tendon and ligament repair, reducing the occurrence of secondary fracture, treating avascular necrosis, facilitating cartilage repair, facilitating bone healing after limb transplantation, facilitating liver regeneration, facilitating wound healing, reducing the occurrence of gastric ulceration, treating hypertension, facilitating the growth of tooth enamel or finger or toe nails, treating glaucoma, treating ocular hypertension, and repairing damage caused by metastatic bone disease using the compounds I [A = SO2, CO; G = Ar, Ar(alkylene), ArCONH(alkylene), etc.; B = N, CH; Q = alkylene, X(alkylene), X(alkylene), etc.; Z = carboxy, alkoxycarbonyl, tetrazolyl, etc.; K = a bond, alkylene, thioalkylene, etc.; M = Ar3, Ar4SAr5, Ar4OAr5, etc.; Ar, Ar3-Ar5 = partially saturated or fully unsaturated 5-8 membered ring having 1-4 heteroatoms selected from O, S, N, or a bicyclic ring, tricycling ring, etc.; X = X = 5-6 membered aromatic ring optionally having 1-2 heteroatoms selected from O, N and S], an EP2 selective receptor agonists. Syntheses of representative compounds I and their intermediates are described in several examples. E.g., a 3-step synthesis of 7-[(4-butylbenzyl)-(pyridine-3-sulfonyl)amino]heptanoic acid, starting from Me 7-aminoheptanoate (preparation given) and 4-butylbenzaldehyde, was given. The compounds I were tested for binding to prostaglandin E2 receptors (data given for exemplified compounds I). The experimental process involved the reaction of Methyl 2-(3-formylphenyl)acetate(cas: 142327-44-4).Electric Literature of 142327-44-4

The Article related to heterocyclic compound ep2 receptor agonist therapeutic antihypertensive, pulmonary hypertension treatment ep2 receptor agonist heterocyclic compound, thiophenecarboxylate preparation ep2 receptor agonist therapeutic antihypertensive, pyridinesulfonylaminomethylphenylacetate preparation ep2 receptor agonist therapeutic antihypertensive and other aspects.Electric Literature of 142327-44-4

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

On May 4, 1984, Makosza, Mieczyslaw; Winiarski, Jerzy published an article.Quality Control of tert-Butyl 2-(4-nitrophenyl)acetate The title of the article was Reactions of organic anions. Part 110. Vicarious nucleophilic substitution of hydrogen in nitroarenes with α-substituted nitriles and esters. Direct α-cyanoalkylation and α-carbalkoxyalkylation of nitroarenes. And the article contained the following:

Carbanions generated from alkanenitriles bearing α-chloro, α-OR (R = Me, Ph, chlorophenyl) or α-SR (R = Me, Ph, Me2NCS) groups and from aliphatic esters bearing α-SR groups react with mononitroarenes to replace H atoms of the nitroarom. ring ortho or para to the NO2 group with α-cyanoalkyl or α-carbalkoxyalkyl substituents. The nucleophilic replacement of H with such carbanions proceeds faster than substitution of halogen ortho or para to the NO2 group. The experimental process involved the reaction of tert-Butyl 2-(4-nitrophenyl)acetate(cas: 29704-38-9).Quality Control of tert-Butyl 2-(4-nitrophenyl)acetate

The Article related to vicarious nucleophilic substitution nitroarene, cyanoalkylation nitroarene, carbalkoxyalkylation nitroarene, nitroarene cyanoalkylation carbalkoxyalkylation, alkylation cyano carbalkoxy nitroarene, alkanenitrile chloro oxy thio anion, chloroalkanenitrile anion reaction, oxyalkanenitrile anion reaction, thioalkanenitrile anion reaction and other aspects.Quality Control of tert-Butyl 2-(4-nitrophenyl)acetate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

On January 25, 2007, Uchida, Hideharu; Kosuga, Naoto; Satoh, Tsutomu; Hotta, Daido; Kamino, Tomoyuki; Maeda, Yoshitaka; Amano, Ken-Ichi; Akada, Yasushige published a patent.Quality Control of tert-Butyl (4-(trifluoromethyl)phenyl)carbamate The title of the patent was Preparation of novel 2-(bicyclic heterocyclidene)acetamide derivatives as antagonists of transient receptor potential type 1 (TRPV1). And the patent contained the following:

The title compounds (I) or salts thereof, and solvates of any of them [m, n, p = an integer of 0-2; q = 0, 1; R1 = halo, each (un)substituted hydrocarbyl, heterocyclyl, C1-6 alkoxy, C1-6 alkoxycarbonyl, NH2, HO, CO2H, CONH2, or SO2NH2, C1-6 alkanoyl, C1-6 alkylthio, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, cyano, NO2; R2 = halo, (un)substituted NH2, hydrocarbyl, or aromatic heterocyclyl, oxo; or two geminal or vicinal R2s together form C2-6 alkylene; R2 and the carbon atom attached to R2 together form a cyclic ring; X1 = O, (un)substituted NH, S, SO, SO2; X2 = CH2, O, (un)substituted NH, S, SO, SO2; Q1 = each (un)substituted heteroaryl, heteroarylalkyl, aryl, or aralkyl; the Cy ring = 5- or 6-membered aryl or heteroaryl; a dotted line represents the condensation of two rings; a wavy line represent E or Z configuration; some exceptions are defined] are prepared These compounds are useful for the treatment or prevention of pains. Thus, tri-Et phosphonoacetate was treated with NaH in THF at ≤20° for 1 h and condensed with 4-chromanone at room temperature overnight to give (E)-(chroman-4-ylidene)acetic acid Et ester which was refluxed in aqueous THF solution containing LiOH and neutralized with 1 N aqueous HCl solution to give (E)-(chroman-4-ylidene)acetic acid (II). II was condensed with 1,4-benzodioxan-6-amine using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride in CH2Cl2 at room temperature overnight to give (E)-2-(chroman-4-ylidene)-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acetamide (III). III and (E)-2-(8-trifluoromethyl-3,4-dihydrobenzo[b]oxepin-5(2H)-ylidene)-N-(quinoxalin-6-yl)acetamide in vitro showed A2 of ≥100 nM and <100 nM, resp., for antagonizing the capsaicin-induced cellular influx of Ca in CHO cell expressing human TRPV1. Pharmaceutical formulations, e.g. a tablet containing (E)-2-(7-tert-Butylchroman-4-ylidene)-N-(5,6,7,8-tetrahydroquinolin-7-yl)acetamide, were prepared The experimental process involved the reaction of tert-Butyl (4-(trifluoromethyl)phenyl)carbamate(cas: 141940-37-6).Quality Control of tert-Butyl (4-(trifluoromethyl)phenyl)carbamate

The Article related to capsaicin receptor trpv1 antagonist bicyclic heterocyclideneacetamide preparation, bicyclic heterocyclideneacetamide preparation antagonist transient receptor potential type 1, chromanylideneacetamide benzooxepinylideneacetamide preparation treatment prevention pain, pain treatment prevention bicyclic heterocyclideneacetamide preparation and other aspects.Quality Control of tert-Butyl (4-(trifluoromethyl)phenyl)carbamate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Sun, Qi; Meng, Xiangju; Liu, Xiao; Zhang, Xiaoming; Yang, Yan; Yang, Qihua; Xiao, Feng-Shou published an article in 2012, the title of the article was Mesoporous cross-linked polymer copolymerized with chiral BINAP ligand coordinated to a ruthenium species as an efficient heterogeneous catalyst for asymmetric hydrogenation.Synthetic Route of 3976-69-0 And the article contains the following content:

Mesoporous ruthenium complexes generated from the copolymer of nonracemic BINAP dioxide bisacrylamide I (or its enantiomer) with divinylbenzene followed by deoxygenation and complexation were prepared as reusable catalysts for chemoselective and enantioselective hydrogenation. In the presence of mesoporous ruthenium complexes generated from the copolymer of I with divinylbenzene, β-keto esters RCOCH2CO2R1 (R = Me, 4-MeOC6H4, ClCH2, Me2CH; R1 = Me, Et, PhCH2, Me3C, Me2CH) were hydrogenated in methanol to the nonracemic β-hydroxy esters II (R = Me, 4-MeOC6H4, ClCH2, Me2CH; R1 = Me, Et, PhCH2, Me3C, Me2CH) in > 99.5% chemoselectivities and conversions and in 91.3-97.7% ee. The surface area of a mesoporous ruthenium complex generated from the copolymer of I and divinylbenzene was determined The mesoporous ruthenium complex generated from the copolymer of I and divinylbenzene was recycled six times in the hydrogenation of Me acetoacetate to give (R)-Me 3-hydroxybutanoate in > 99.5% chemoselectivities and conversions and in 91.3-95.3% ee. Copolymers of other vinyl-functionalized nonracemic ligands with divinylbenzene were prepared; transfer hydrogenation of acetophenone in the presence of a (R,R)-N-(4-vinylphenylsulfonyl)-1,2-diphenyl-1,2-ethanediamine-divinylbenzene copolymer ruthenium complex gave 1-phenylethanol in 94% ee. The experimental process involved the reaction of (R)-Methyl 3-hydroxybutanoate(cas: 3976-69-0).Synthetic Route of 3976-69-0

The Article related to mesoporous copolymer binap bisacrylamide ruthenium complex enantioselective hydrogenation catalyst, vinyl functionalized ligand copolymer ruthenium complex enantioselective hydrogenation catalyst, beta hydroxy ester enantioselective preparation, enantioselective hydrogenation beta ketoester binap bisacrylamide copolymer ruthenium complex and other aspects.Synthetic Route of 3976-69-0

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

On August 4, 2016, Dejesus, Reynalda K.; Fu, Qinghong; Jiang, Jinlong; Tang, Haifeng published a patent.Synthetic Route of 1198284-94-4 The title of the patent was Preparation of novel spirocyclic compounds as inhibitors of the renal outer medullary potassium channel. And the patent contained the following:

The title compounds I [R1 = H, halo, OH, alky, alkoxy; R2 = H, alkyl; R3 = H, or alkyl optionally substituted with OH, OMe or 1-3 halo; or R3 and R4 are joined together to form CH2CH2; R4 = H, or alkyl optionally substituted with OH, OMe or 1-3 halo; n = 1-2; m = 1-2, wherein when m = 2, X3 = CH2; R5 = H, halo, cycloalkyl or alkyl; X1 = C(O), CH2; X2 = O, CH2; X3 = C(O), CH2, wherein when X3 = CH2, m = 2;X4 = C(O), SO2; Z = II or III (Y1-Y4 = (independently) CR9 or N; provided that at most two of Y1-Y4 are N; R9 = (independently) H, halo, alkoxy or alkyl optionally substituted with 1-3 halo; R10 = H, halo, alkyl optionally substituted with 1-3 halo; R11 = H, alkyl optionally substituted with 1-3 halo; R12 = H or alkyl)] which are inhibitors of the ROMK (Kir1.1) channel, were prepared For example, microwaving a solution of (1R,3r,5S)-1′-(2-methyl-3-oxocyclopent-1-en-1-yl)-8-azaspiro[bicyclo[3.2.1]octane-3,3′- pyrrolidin]-2′-one and (R)-4-methyl-5-(oxiran-2-yl)isobenzofuran- 1(3H)-one in EtOH at 145°C for 4.5 h afforded IV. Exemplified compounds I were tested in the thallium flux assay (data given). The compounds I may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and chronic kidney disease and conditions associated with excessive salt and water retention. Pharmaceutical compositions comprising I, alone or in combination with other therapeutic agent, are disclosed. The experimental process involved the reaction of tert-Butyl 1-oxo-2,9-diazaspiro[5.5]undecane-9-carboxylate(cas: 1198284-94-4).Synthetic Route of 1198284-94-4

The Article related to spirocyclic compound preparation renal outer medullary potassium channel inhibitor, romk inhibitor diuretic natriuretic cardiovascular antihypertensive spirocyclic compound preparation, heart failure chronic kidney disease treatment spirocyclic compound preparation, excessive salt water retention treatment spirocyclic compound preparation and other aspects.Synthetic Route of 1198284-94-4

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Burghart-Stoll, Heike; Brueckner, Reinhard published an article in 2012, the title of the article was Total Syntheses of the Gregatins A-D and Aspertetronin A: Structure Revisions of These Compounds and of Aspertetronin B, Together with Plausible Structure Revisions of Gregatin E, Cyclogregatin, Graminin A, the Penicilliols A and B, and the Huaspenones A and B.Category: esters-buliding-blocks And the article contains the following content:

Comprehensive comparisons of 1H and 13C NMR chem. shift values in the furanone cores a, b, and c provide plausible support for a reassessment of the furanone nuclei of the title compounds from b to c. Total syntheses via enantiomerically pure lactic esters were based on the Seebach-Frater “self-reproduction of stereocenters” methodol. Attachment of the hexadienyl side-chain in a trans,trans-selective manner was achieved by addition of the Seebach-Frater enolate to trans-hex-4-en-1-al rather than to trans-hex-3-en-1-al. The type-c furanone cores of the synthetic materials were reached by single or double acylation of model γ-hydroxy-β-oxo ester I and its hexadiene-containing counterpart II. Our syntheses confirmed the novel connectivities in six compounds In addition, they required revision of the configuration of a quaternary carbon atom in five cases. Moreover, they allowed elucidation of the configurations of four previously unassigned stereocenters. Hindsight analyses of why the furanone cores of the title compounds had been misinterpreted as a and/or b instead of c are given. Why the stereocenters in the heterocycles had been incorrectly configured, on the bases (a) of relay studies in the 1960s, and (b) of a 1984 total synthesis of gregatin B, is also discussed. The experimental process involved the reaction of (R)-Methyl 3-hydroxybutanoate(cas: 3976-69-0).Category: esters-buliding-blocks

The Article related to synthesis lactic ester gregatin aspertetronin, mol structure revision gregatin graminin aspertetronin penicilliol huaspenone cyclogregatin, nmr chem shift mol structure revision furanone derivative, seebach frater self reproduction stereocenters methodol synthesis gregatin aspertetronin, hexadienyl side chain addition trans selective manner and other aspects.Category: esters-buliding-blocks

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

On June 10, 2004, Fujimoto, Roger Aki; McQuire, Leslie Wighton; Monovich, Lauren G.; Mugrage, Benjamin Biro; Parker, David Thomas; Van Duzer, John Henry; Wattanasin, Sompong published a patent.Formula: C12H14F3NO2 The title of the patent was Preparation of substituted amino phenylacetic acids and derivatives and their use as cyclooxygenase-2 (COX-2) inhibitors. And the patent contained the following:

The title compounds I (R = H, alkyl, cycloalkyl, halo, alkoxy, F3CO, Me3C, cyano, R1 = biaryl, β-naphthyl derivative, bicyclic heterocyclic aryl, cycloalkyl monocyclic carbocyclic aryl, cycloalkane fused-monocyclic carbocyclic aryl) were prepared Thus, N,N-dimethyl-2-(2′,3′,5′,6′-tetrafluoro-4′-phenylanilino)phenylacetamide was hydrolyzed to give I (R = H, R1 = 4-PhC6F4). The experimental process involved the reaction of tert-Butyl (4-(trifluoromethyl)phenyl)carbamate(cas: 141940-37-6).Formula: C12H14F3NO2

The Article related to phenylacetic acid amino preparation cyclooxygenase 2 inhibitor, rheumatoid arthritis inhibitor aminophenylacetic acid, osteoarthritis inhibitor aminophenylacetic acid, dysmenorrhea inhibitor aminoophenylacetic acid, pain inhibitor aminophenylacetic acid, neoplasm inhibitor aminophenylacetic acid, inflammation inhibitor aminophenylacetic acid and other aspects.Formula: C12H14F3NO2

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Wu, Binyu; Wen, Xiaolu; Chen, Hongbing; Hu, Lin published an article in 2021, the title of the article was N-Nosyl-O-bromoethyl hydroxylamine acts as a multifunctional formaldehyde, formaldimine, and 1,2-oxazetidine surrogate for C-C and C-O bond-forming reactions.Application of 10472-24-9 And the article contains the following content:

N-Nosyl-O-bromoethyl hydroxylamine, a bench stable solid, could function as a novel formaldehyde, formaldimine and 1,2-oxazetidine surrogate under DBU basic conditions were described. By merely using this simple reagent, a broad range of synthetically useful β-aminomethyl ketones I [R1 = Me, Ph, 2-furyl, etc.; R2 = Me, Et, allyl, Bn; R1R2 = (CH2)3, (CH2)4, (CH2)5, etc.; R3 = Ac, CO2Me, CO2Et, SO2Ph] and α-hydroxymethyl ketones II [R4 = Me, Et, allyl, Bn; Q = (CH2)n, n = 1,2], as well as chiral α-alkoxyl indanone carboxylates III [R5 = H, 4-MeO, 5-F, etc.; X = OCH2CH2] and α-aminomethyl indanone carboxylates III [X = CH2] could be divergently obtained via chemo- and stereoselective aldol, Mannich or umpolung C-O bond-forming reactions. The challenging catalytic asym. Mannich reaction of formaldimine equivalent was also realized with moderate enantioselectivities. The experimental process involved the reaction of Methyl 2-cyclopentanonecarboxylate(cas: 10472-24-9).Application of 10472-24-9

The Article related to aminomethyl ketone preparation, nosyl bromoethyl hydroxylamine benzoyl acetate bond formation, hydroxymethyl ketone preparation, hydroxy ketone nosyl bromoethyl hydroxylamine bond formation, carboxylate indanone hydroxymethyl preparation enantioselective chemoselective, alkoxyl indanone carboxylate preparation enantioselective chemoselective and other aspects.Application of 10472-24-9

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

On April 5, 2021, Zhao, Huaibo; Leonori, Daniele published an article.Reference of Methyl N-Methylanthranilate The title of the article was Minimization of Back-Electron Transfer Enables the Elusive sp3 C-H Functionalization of Secondary Anilines. And the article contained the following:

Anilines are some of the most used class of substrates for application in photoinduced electron transfer. N,N-Dialkyl-derivatives enable radical generation α to the N-atom by oxidation followed by deprotonation. This approach is however elusive to monosubstituted anilines owing to fast back-electron transfer (BET). Here we demonstrate that BET can be minimised by using photoredox catalysis in the presence of an exogenous alkylamine. This approach synergistically aids aniline SET oxidation and then accelerates the following deprotonation. In this way, the generation of α-anilinoalkyl radicals is now possible and these species can be used in a general sense to achieve divergent sp3 C-H functionalization. The experimental process involved the reaction of Methyl N-Methylanthranilate(cas: 85-91-6).Reference of Methyl N-Methylanthranilate

The Article related to arylamine arylpyrrolidinone aminobenzonitrile chemoselective photochem preparation, iridium cobalt photoredox catalyst dealkylation addition arylation base mediated, inhibition back electron transfer photochem dealkylation addition alkylarylamine, c−h functionalization, anilines, electron transfer, late-stage modification, photoredox catalysis and other aspects.Reference of Methyl N-Methylanthranilate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

On October 8, 2009, Matsunaga, Nobuyuki; Nakada, Yoshihisa; Ohba, Yusuke; Nakagawa, Hideyuki published a patent.Quality Control of Ethyl 3-fluoro-4-methylbenzoate The title of the patent was Preparation of pyrazole-containing heterocyclic compound derivatives as soluble guanylyl cyclase (sGC) activators. And the patent contained the following:

The title compounds [I; ring A1 = each (un)substituted aromatic hydrocarbon or 5- or 6-membered aromatic heterocyclic ring; ring B1 = each (un)substituted 5-membered aromatic heterocyclic ring or 5-membered aromatic heterocyclic ring- or 5- or 6-membered carbocyclic ring-fused heterocyclic ring; D1 = each (un)substituted aromatic hydrocarbon or aromatic heterocyclic ring; R1 = CO2H, tetrazolyl, oxooxadiazolyl, C(O)NHS(O)2R11; R11 = acyl, each (un)substituted lower alkyl or aromatic hydrocarbyl or 5- or 6-membered aromatic heterocyclyl; X1 = a bond, (un)substituted lower alkylene; Y1 = a bond, (un)substituted lower alkylene, L1a-E1-L1b; L1a, L1b = a bond, (un)substituted lower alkylene; E1 = O, S, S(O)< S(O)2, C(O), each (un)substituted NH, C(O)NH, NHC(O), S(O)NH, or NHS(O)2; some provisos are applied.] or salts thereof or prodrugs thereof were prepares There is specifically disclosed an soluble guanylyl cyclase (sGC) activator comprising the compound I or a salt thereof as an active ingredient. The compounds I are soluble guanylyl cyclase (sGC) activators and are useful for the prevention or treatment of diseases including hypertension, ischemic heart diseases, heart failure, kidney diseases, arteriosclerotic diseases, atrial fibrillation, pulmonary hypertension, diabetes, diabetic complications, metabolic syndrome, peripheral arterial disease and erectile dysfunction. They have excellent pharmacol. activities, excellent physicochem. properties, and others. Thus, a solution of 2.99 g Et 1-(2-amino-2-thioxoethyl)-1H-pyrazole-4-carboxylate in 30 mL ethanol was treated with 3.74 g 2-bromo-1-[3-(trifluoromethyl)phenyl]ethanone and refluxed for 14 h to give, after workup and silica gel chromatog., 91% Et 1-([4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]methyl)-1H-pyrazole-4-carboxylate (II). II (4.80 g) was treated with 40 mL ethanol, 10 mL THF, and 12.6 mL 2 N aqueous NaOH solution, stirred overnight, concentrated under reduced pressure, treated with water, washed with ether, and acidified with 6 N aqueous HCl solution to give, after workup and recrystallization from EtOAc and hexane, 67% 1-([4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]methyl)-1H-pyrazole-4-carboxylic acid (III). III in vitro promoted >1,000% the production of cGMP from guanosine 6′-triphosphate in the presence of sGC. III at 30 mg/kg in vivo lowered blood pressure by 15.5 mmHg in male SHR mice after 5 h. A capsule formulation containing III was described. The experimental process involved the reaction of Ethyl 3-fluoro-4-methylbenzoate(cas: 86239-00-1).Quality Control of Ethyl 3-fluoro-4-methylbenzoate

The Article related to thiazolylmethylpyrazolecarboxylic acid preparation soluble guanylyl cyclase activator, pyrazole containing heterocyclic preparation soluble guanylyl cyclase sgc activator, hypertension ischemic heart disease treatment pyrazole containing heterocyclic preparation, heart failure kidney disease treatment pyrazole containing heterocyclic preparation and other aspects.Quality Control of Ethyl 3-fluoro-4-methylbenzoate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics