Tag: M.W=200-300

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate

To a stirred solution of (E)-5-((4-chlorobenzylidene)amino)-1,3-dimethylpyridin-2(1H)-one (Step 73.1) (4 g, 15.34 mmol) in AcOH (40 mL) was added diethyl oxaloacetate sodium salt (6.45 g,30.7 mmol) and the resulting mixture was heated up and stirred at 110 00 for 1 hr. The reactionwas concentrated under reduced pressure, diluted with CH2CI2 and water and both phases separated. The aqueous layer was extracted twice with CH2CI2, combined organic layers were washed with brine, dried over Na2504, filtered and concentrated under reduced pressure. The crude product was triturated in Et20 to afford the title product (4.42 g, 8.34 mmol, 54% yield) as beige solid. tR: 0.86 mm (LC-MS 2); ESl-MS: 403 [M+H], ESl-MS: 401 [M-H] (LC-MS 2).

According to the analysis of related databases, 40876-98-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; BLANK, Jutta; BORDAS, Vincent; COTESTA, Simona; GUAGNANO, Vito; RUEEGER, Heinrich; VAUPEL, Andrea; WO2014/191896; (2014); A1;,
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Synthetic Route of 29263-94-3,Some common heterocyclic compound, 29263-94-3, name is Diethyl 2-bromo-2-methylmalonate, molecular formula is C8H13BrO4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a 7 mL vial equipped with magnetic stir bar was added bromomalonate (1.0 equiv,0.40 mmol), 2,6-lutidine (1.0 equiv, 0.40 mmol), tris[2-phenylpyridinato-C2,N]iridium(III) (1 mol %, 4.0 mumol), and heterocycle (5.0 equiv, 2.0 mmol). Dryacetonitrile or DMA (0.5 mL, 0.8 M) was then added and the reaction was sparged withN2 for 15 min. The reaction was set to stir under nitrogen at room temperature surroundedby a string of 1W or two strings of 4W blue LEDs for 24 h. The reaction mixture wasthen diluted with ethyl acetate and extracted with water. The aqueous layer was extractedwith ethyl acetate (2 x 10 mL). The combined organic layers were washed with brine,dried over Na2SO4, and concentrated in vacuo. The residue was purified bychromatography on silica gel, using the solvent system indicated.

The synthetic route of 29263-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Swift, Elizabeth C.; Williams, Theresa M.; Stephenson, Corey R. J.; Synlett; vol. 27; 5; (2016); p. 754 – 758;,
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Related Products of 65868-63-5, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 65868-63-5, name is tert-Butyl 6-bromohexanoate, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of tert- butyl 6-bromohexanoate (1 .0 g, 3.98 mmol) in THF (10 mL) was added dimethylamine (2 M in THF) (7.96 mL, 15.93 mmol). The reaction mixture was stirred at room temperature for 16 h. The resulting mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography, eluting with a gradient 1 % – 15% MeOH in DCM. The fractions containing the desired product were combined and concentrated to afford Z-2. LC/MS: (M+H)+ = 216.2. 1H NMR (300 MHz, CDCIs): d 2.35-2.17 (m, J = 8.5, 6.5 Hz, 10H), 1.67-1.47 (m, 4H), 1.45 (s, 9H), 1.42 -1.23 (m, 2H).

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 6-bromohexanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WOOD, Harold, B.; JOSIEN, Hubert, B.; TUCKER, Thomas, Joseph; KEREKES, Angela, Dawn; TONG, Ling; WALJI, Abbas, M.; NAIR, Anikumar, G.; DING, Fa-Xiang; BIANCHI, Elisabetta; BRANCA, Danila; WU, Chengwei; XIONG, Yusheng; HA, Sookhee, Nicole; LIU, Jian; BOGA, Sobhana, Babu; (183 pag.)WO2019/246349; (2019); A1;,
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Electric Literature of 82702-31-6, A common heterocyclic compound, 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate, molecular formula is C8H6BrFO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of methyl 3 -bromo-4-fluorobenzoate (0.280 g, 1.2 mmol), Example 28b (0.211 g, 1.200 mmol), and cesium carbonate (0.391 g, 1.200 mmol) in dimethyl sulfoxide (5 mL) was heated at 110 C overnight. After cooling, the reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethylacetate three times. The combined organic layers were washed with brine, separated, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica eluting with 20% ethyl acetate in heptanes to provide the title compound (0.08 g, 0.206 mmol, 17.1 % yield).

The synthetic route of 82702-31-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; FIDANZE, Steven D.; HASVOLD, Lisa A.; LIU, Dachun; MCDANIEL, Keith F.; PRATT, John; SCHRIMPF, Michael; SHEPPARD, George S.; WANG, Le; LI, Bing; (191 pag.)WO2017/177955; (2017); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 107045-28-3, name is tert-Butyl 4-(aminomethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C12H17NO2

46.4 g (200 mmol) of 4-chloro-1,8-naphthalic anhydride and 41.4 g (200 mmol) of tert-butyl 4-aminomethylbenzoate were placed in 250 mL of EtOAc to form a suspension.Stir at RT for 16 hours.The resulting precipitate was filtered and dried at 50 C for 8 hours.A white powder of 48 g (yield 57%) was obtained.

According to the analysis of related databases, 107045-28-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Institute of Biophysics, Chinese Academy of Sciences; Suzhou Shoutong Science And Technology Co., Ltd.; Dai Yu; Zhao Jianyong; Zhang Wenxin; (21 pag.)CN108675989; (2018); A;,
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Related Products of 541-16-2, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 541-16-2 as follows.

Compound 168 (80 mg, 0.14 mmol) was dissolved in 10 mL of acetonitrile and iodomethane (86 [mu] L, 1.39 mmol) was added and reacted at room temperature for 24 hours.The reaction solution is directly concentrated,The compound 168 was rinsed with a 50 mL mixture of petroleum ether: dichloromethane = 4: 1 (v / v)Of the imidazole moiety of iodomethane salt 75 mg, yield 76%; A tryptamine (2.0 g, 12.5 mmol) was dissolved in 20 mL of tetrahydrofuran,(3.5 mL, 25 mmol) and tert-butoxycarboxylic anhydride (3.03 g, 15.0 mmol) were added in turn followed by reaction at 10 C for 1 hour,The reaction solution was poured into 100 mL of ice water and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, concentrated by flash column chromatography, and eluted with petroleum ether: ethyl acetate = 2: 1 (v / v) to give N- [2- (3-indole) ethyl] carbamic acid tert-butyl ester, yield 97%;A solution of tert-butyl N- [2- (3-indole) ethyl] carbamate(1.8 g, 6.92 mmol) was dissolved in 110 mL of THF / H2O (10: 1)Down to 0 C,DDQ (3.1 g, 13.8 mmol) was added and reacted at this temperature for two hours.The reaction solution was poured into 200 mL of ethyl acetate and washed with saturated sodium bicarbonate solution to a colorless color,The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated. The column was separated by flash column chromatography,Petroleum ether: ethyl acetate = 1: 1 (v / v)2- [3-oxo-2- (3-indole) ethyl] carbamate in a yield of 63%A solution of tert-butyl N- [2-oxo-2- (3-indole) ethyl] carbamate (200 mg, 0.73 mmol)Treated with 5 mL of trifluoroacetic acid, reacted at 10 C for one hour,Benzene (5 mL x 3 times) was obtained by azeotropic removal of trifluoroacetic acidN- [2-oxo-2- (3-indole) ethyl] trifluoroacetic acid in 185 mg, yield 93%.(75.0 mg, 0.105 mmol) of the imidazole moiety of compound 168 was dissolved in 2 mL of DMF and triethylamine (73.0 [mu] L, 0.525 mmol) and N- [2-oxyadienyl-2- (3-indole(85.4 mg, 0.315 mmol, 3.0 equiv) was added and reacted at room temperature for 24 hours.The reaction solution was diluted with 10 mL of ethyl acetate, washed with 1N hydrochloric acid,Dried over anhydrous sodium sulfate and concentrated.Semi-preparative HPLC separation, MeOH: H2O = 9: 1 (v / v)Eluting to give 40 mg of 3′-N- [N- (2-oxo-2- (3-indolyl) ethyl) aminothioformyl] staurosporine (169) in 56% yield.

According to the analysis of related databases, 541-16-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ocean University of China; Key Laboratory of Chemistry for Natural Products of Guizhou Province Chinese Academy of Sciences; Zhu, Weiming; Ma, Hongguang; Wang, Liping; Xu, Zhihong; Zhang, Yapeng; Wang, Yi; Liu, Peipei; (142 pag.)CN106083830; (2016); A;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 151583-29-8, name is Methyl 3-(3-bromophenyl)propanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C10H11BrO2

Example 37B: 3-(3-methoxy-3-oxopropyl)phenylboronic acid j00413j DMSO (6.86 mL) and dioxane (6.86 mL) were degassed for 15 mm bybubbling with argon. Meanwhile, Example 37A (400 mg, 1.645 mmol), KOAc (404 mg,4.11 mmol), and bis(neopentyl glycolato)diboron (520 mg, 2.304 mmol) were placed in amicrowave tube. To these compounds was added the degassed solvents. The tube was sealed and degassed for an additional 15 mi [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (135 mg, 0.165 mmol) was subsequently added, the tubesealed, and heated to 90 C and allowed to stir overnight. The reaction was diluted withEtOAc and washed twice with brine, dried (Na2SO4), filtered, and concentrated in vacuo.The crude reaction mixture was purified by Prep LC (Axia Luna 5 t Cl 8 3 Ox 100 mmcolumn, 10 mm gradient from 40 to 100% B in A, A = 10:90:0.1 MeCN:H20:TFA, B =90:10:0.1 MeCN:H20:TFA) to yield Example 37B (O.224g, 64%) which was usedimmediately after purification.

The synthetic route of 151583-29-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; RICHTER, Jeremy; BATES, J. Alex; CHENEY, Daniel L.; WO2014/201073; (2014); A1;,
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Electric Literature of 124-06-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 124-06-1, name is Ethyl tetradecanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(Example 4) Synthesis of N-[2-(1-methylpyrrolidin-2-yl)ethyl]myristamide (Compound 4) toluene (1.00 ml), dried using MS 4A, was mixed with 1.00 ml of a n-hexane solution of 15% Me3Al. With the mixture being cooled in an ice-methanol bath, 0.17 ml (0.78 mmol) of 2-(2-aminoethyl)-1-methylpyrrolidine was added dropwise over about 2 minutes.. After stirring for 20 minutes, the temperature was raised to room temperature, and 0.5 ml of a toluene solution of 0.2 g (0.78 mmol) of myristic acid ethyl ester was added dropwise over 1 minute.. After stirring for 2 hours at 70C, the mixture was cooled with ice, and a 1N NaOH solution was added dropwise.. The mixture was stirred for 10 minutes, and water and ethyl acetate were added.. Then, the mixture was separated into respective layers, and the organic layer was washed twice with 20 ml of a saturated aqueous solution of sodium chloride.. After this layer was dried over anhydrous magnesium sulfate, it was concentrated under reduced pressure on a 30C water bath to obtain the captioned compound (yield 0.25 g).. This compound was subjected to silica gel column chromatography (mobile phase: CHCl3:MeOH (19:19:1)) for purification. NMR and mass spectrum confirmed the purified compound to have the following structure:

The synthetic route of Ethyl tetradecanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Maruha Corporation; EP1408030; (2004); A1;,
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Synthetic Route of 35120-18-4, A common heterocyclic compound, 35120-18-4, name is Ethyl 1-bromocyclobutanecarboxylate, molecular formula is C7H11BrO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

7-bromoquinoline-4-thiol 31b (220 mg, 0.90 mmol), ethyl 1-bromocyclobutanecarboxylate (227 mg, 1.10 mmol) and cesium carbonate (896 mg, 2.70 mmol) were added to 5 mL of NA-dimethylformamide, successively. The reaction solution was heated to 60 C. and stirred for 2 hours, then mixed with 50 mL of water, stirred uniformly, and extracted with ethyl acetate (50 mL*3). The organic phases were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by thin layer chromatography with elution system C to obtain the title compound ethyl 1-((7-bromoquinolin-4-yl)thio)cyclobutanecarboxylate 31c (100 mg, a colorless oil) yield: 30%. MS m/z (ESI): 368.1 [M+1]

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co., Lt.d; PENG, Jianbiao; SUN, Piaoyang; LAN, Jiong; GU, Chunyan; LI, Xiaotao; LIU, Bonian; HAN, Chunzhou; HU, Qiyue; JIN, Fangfang; DONG, Qing; CAO, Guoqing; (57 pag.)US2016/108035; (2016); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1236357-65-5, name is Methyl 1-(4-bromophenyl)cyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C12H13BrO2

To a 25 mL round-bottom t1ask purged with and maintained under an inertatmosphere of nitrogen was added (1 S,4S,5R)-.5-[ [ 5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2- oxazol-4-yl]methoxy ]-2-az.abicyclo[ 2.2.l]heptane hydroiodide salt l2dd (200 mg, 0.3943rnmol, 1.00 equiv.), Tol (lO mL), methyll-(4-bromophenyl)cyclobui:me-1-carboxylate 150b(212 mg, 0.79 mmol, 2.0 equiv.), Ru-Phos-Precatalyst (89 mg, 0.10 mmol, 0.25 equiv.),RuPhos (89 mg), and Cs2C01 (516 mg, 1.58 mmol, 4.00 equiv.). The resulting mixture was5 stirred at ll 0 C overnight and concentrated under vacuum. The residue vvas puriiled bysilica gel column chromatography eluting with ethyl acetate/petroleum ether (l/5) to affordmethyl 1-[4-[ (l S,4S,5R)-5-[ [ 5-cyclopropyl-3-(2,6-dichlorophenyl)- L2-oxazol-4-y l]methoxy ]-2-azabicydo[2.2.1]heptan-2-yl]pheny l]cyclobutane-1-carboxy late 150c (140rng, 63~”0) as a light yellow oil.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1236357-65-5.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
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