Month: February 2021

Electric Literature of 53518-15-3, 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. 53518-15-3, name is 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 159 8-Hydroxy-N-[4-(trifluoromethyl)coumarin-7-yl]-7-quinolinecarboxamide monohydrochloride (V-11) (Refer to Chart V): According to GP II, starting from anhydride U-1 (200 mg), pyridinium chloride (42 mg), 7-amino-4-(trifluoromethyl)coumarin (85 mg) and CHCl3 (8 mL), amide V-11 is obtained as a yellow powder (25 mg). Physical characteristics are as follows: 1H-NMR (d6-DMSO, 300 MHz) delta 8.94, 8.65, 8.11, 8.05, 7.83, 7.71, 7.66, 7.38, 6.91. 13C-NMR (d6-DMSO, 75 MHz) delta 166.40, 159.13, 155.28, 146.35, 143.73, 140.72, 131.77, 128.52, 125.91, 124.11, 117.29, 116.40, 114.67, 114.57, 108.91, 107.41. MS (EI) m/z 400 (M+), 172, 116, 89.

The chemical industry reduces the impact on the environment during synthesis 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Pharmacia & Upjohn Company; US6211376; (2001); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 383-62-0, name is Ethyl 2-chloro-2,2-difluoroacetate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 383-62-0

Example 1Production of alpha-silyl difluoroacetic acid ester (1) According to the above-described scheme, magnesium (243 mg, 10.0 mmol), chlorotrimethylsilane (Me3SiCl; 2.17 g, 20.0 mmol) and DMF (15 mL) were put into a two-neck reaction tube under nitrogen atmosphere. Ethyl chlorodifluoroacetate (Compound 3; 793 mg, 624 muL, 5.0 mmol) was added thereto with the reaction container being cooled in water bath, and then the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was extracted with diethyl ether and washed with water, and an organic layer was dried with anhydrous sodium sulfate. Diethyl ether was distilled away under reduced pressure, and by carrying out the production by silica gel column chromatography, difluorotrimethylsilanylacetic acid ethyl ester (Compound 3a) was obtained with a yield of 43%.Note that in other working examples, as difluorotrimethylsilanylacetic acid ethyl ester (Me3Si-CF2CO2Et; Compound 3a), the product obtained in this working example was used.The results of instrumental analysis of the product (Compound 3a) are shown below:1H-NMR (CDCl3, TMS) delta4.32 (2H, q, J=7.0 Hz), 1.35 (3H, t, J=7.0 Hz), 0.237 (9H, s) 19F-NMR (CDCl3, C6F6) delta38.5 (2F, s) Mass m/e: (m/z) (%) 181 (6), 153 (10), 125 (6), 103 (8), 77 (26), 73 (100)

According to the analysis of related databases, 383-62-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Amii, Hideki; Fujikawa, Kenichi; Fujioka, Yasutaka; Matsuura, Makoto; US2012/220795; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

6914-71-2, name is 1,1-Cyclopropanedicarboxylic acid dimethyl ester, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 1,1-Cyclopropanedicarboxylic acid dimethyl ester

Comparative Example 1; According to the same manner as that described in Example 3, the reaction did not proceed and (S)-tert-leucinol and dimethyl cyclopropanedicarboxylate, which are starting materials, were recovered except that lithium methoxide was not used in Example 3.

The synthetic route of 6914-71-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP1698617; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, molecular formula is C10H7FO2, 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. Product Details of 42122-44-1

EXAMPLE 1 Intermediate A To a solution of methyl 4-(fluorophenyl)propynoate (J. Org. Chem. 1987, 52(16), 3662-8) (13 g, 73 mmol) in methanol (60 ml) was added water (60 ml) followed by methylhydrazine (4 ml, 77 mmol), the mixture was stirred for 6 hrs at 60 C. then left to stand overnight. The solid was filtered and washed with water then a minimum volume of methanol and dried overnight, affording 7.7 g of 5-(4-fluorophenyl)-1-methyl-1,2-dihydropyrazol-3-one (55%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 42122-44-1, its application will become more common.

Reference:
Patent; Castro Pineiro, Jose Luis; Collins, Ian James; Harrison, Timothy; US2005/143369; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 42726-73-8, name is tert-Butyl methyl malonate, 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. Formula: C8H14O4

EXAMPLE 125 Diethyl 2,2-Difluoroglutarate (b) Diethyl 2-ketoglutarate (a, 10.06 g, 49.74 mmol), methylene chloride (150 ml), and water (0.5 ml) were combined in a stainless steel bomb under N2 and cooled to -78. Sulfur tetrafluoride (~90 g, 833 mmol) was condensed in a polypropylene bottle at -78 and added to the reaction mixture. The bomb was sealed, then allowed to come to room temperature. After a total of 20 hrs, the bomb was vented through aqueous sodium hydroxide. The reaction mixture was worked up with methylene chloride, washing with aqueous sodium bicarbonate and brine. It yielded 11.38 g of crude yellow oil containing a white solid material. The white solid was filtered off and the oil distilled under reduced pressure through a Vigreux column. (bp 82-95, 5 mm). Total yield 6.27 g (57%) of the title compound as a light yellow oil. Silica gel tlc: Rf 0.47 in EtOAc:Hexane 1:3,

The synthetic route of tert-Butyl methyl malonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The University of Chicago; US4324730; (1982); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 150529-73-0, category: esters-buliding-blocks

Tributyltin methoxide (28.3 mL, 98 mmol), preparation 25 (15.0 g, 65 mmol), isopropenyl acetate (10.8 mL, 98 mmol), palladium(II)acetate (750 mg, 3.30 mmol) and tri-ortho-tolylphosphine (2.0 g, 6.5 mmol) were stirred together in toluene (75 mL) at 100 C. under nitrogen for 5 hours. After cooling the reaction was diluted with ethyl acetate (150 mL) and 4M aqueous potassium fluoride solution (90 mL) and stirred for 15 minutes. The mixture was filtered through arbocel and the organic phase separated and reduced in vacuo. The residue was purified by flash column chromatography silica gel eluting with a solvent gradient of diethyl ether:pentane (0:100 to 25:75, by volume) changing to dichloromethane to give the title compound as a pale yellow oil (12.6 g). 1H NMR (400 MHz, CDCl3): delta=7.30 (1H, t), 7.19 (1H, d), 7.13-7.10 (2H, m), 3.69 (5H, s), 3.61 (2H, s), 2.15 (3H, s) ppm. LRMS (electrospray): m/z [M+NH4]+224, [M+Na]+229.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 2-(3-bromophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc; US2005/222128; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 10259-22-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 10259-22-0 name is Ethyl 3-methoxybenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

a) 3 -(3 -Me thoxy -phenyl) – 3 – oxo-prop ion Ur UeTo a solution of commercially available 3-methoxy-benzoic acid ethyl ester (3.2 g, 18 mmol) in dry toluene (25 mL), under N2, NaH (50-60% dispersion in mineral oil, 1.44 g. 36 mmol) was carefully added. The mixture was heated at 9O0C and anhydrous CH3CN was added dropwise (4.45 mL, 85.2 mmol). The reaction was heated for 18 hours and the product precipitated from the reaction mixture as Na salt. The reaction was allowed to cool down to room temperature and the solid formed was filtered and washed with ether, then it was redissolved in water and the solution acidified with 2N HCl solution to pH 3 when precipitation of title compound was observed. Filtration of the solid from the aqueous solution afforded 1.57 g of title product (50% yield).C10H9NO2Mass (calculated) [175]; (found) [M+H~] =176LC Rt = 1.69, 94% (5 min method)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Patent; SIENA BIOTECH S.P.A.; WYETH PHARMACEUTICALS; WO2008/87529; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate

Acetylenedicarboxylic acid (0.35 g, 3.09 mmol, 1.0 eq. ) was dissolved in NMP (10 mL) and cooled to 0 , to which compound tert-butyl 3- (2- (2- (2-aminoethoxy) ethoxy) ethoxy) -propanoate (2.06 g, 7.43 mmol, 2.4 eq. ) was added, followed by DMTMM (2.39 g, 8.65 mmol, 2.8 eq. ) in portions. The reaction was stirred at 0 for 6 h and then diluted with ethyl acetate and washed with water and brine. The organic solution was concentrated and triturated with a mixture solvent of ethyl acetate and petroleum ether. The solid was filtered off and the filtrate was concentrated and purified by column chromatography (80-90%EA/PE) to give a light yellow oil (2.26 g, >100%yield) , which was used without further purification. MS ESI m/z [M+H] + 633.30.

The synthetic route of 252881-74-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HANGZHOU DAC BIOTECH CO., LTD; ZHAO, Robert Yongxin; ZHUO, Xiaotao; YANG, Qingliang; ZHAO, Linyao; HUANG, Yuanyuan; YE, Hangbo; YANG, Chengyu; LEI, Jun; GAI, Shun; GUO, Huihui; JIA, Junxiang; BAI, Lu; XIE, Hongsheng; ZHOU, Xiaomai; GUO, Zhixiang; LI, Wenjun; CAO, Mingjun; ZHENG, Jun; YE, Zhichang; YANG, Yanlei; (325 pag.)WO2020/6722; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 103-25-3, name is Methyl 3-phenylpropionate, molecular formula is C10H12O2, 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. Formula: C10H12O2

General procedure: A mixture of Lithium aluminum hydride (9.5 g, 0.250 mol), dry THF(250 mL), to it add substituted dihydrocinnamic acid methyl ester (3ae,0.127 mol), in THF (50 mL) was added slowly drop wise during30 min. After completion of addition the reaction mixture was stirredfor 2 h at rt, after completion of reaction as monitored by TLC hexane/ethyl acetate (8:2), the reaction mixture was poured in water (200 mL),acidified with 5 N HCl, extract with chloroform (2¡Á400 mL), extractwas wash with water, brine solution, dried over Na2SO4 and concentrated.The crude residue was subjected to column chromatographyon silica gel, column was eluted with hexane/ethyl acetate mixtures,pure compound was eluted in ethyl acetate in hexane, 10%/90% (v/v)which was monitored by TLC, pure fractions were combined and concentratedto obtained 3-(substituted phenyl)- propan-1-ol as oily compoundswith yields of 73-77%. 3.2.13 3-(Phenyl)-propan-1-ol (4a) Weight: 9.10?g; % yield: 73.2%; 1H NMR (CDCl3, 400?MHz): delta 7.32-7.28 (2H, m, H-3′, 5′), 7.14 (2H, d, J?=?8.0?Hz, H-2′, 6′), 7.06 (1H, t, J?=?7.2?Hz, H-4′), 3.56 (2H, t, J?=?8.0?Hz, CH2), 2.56 (2H, t, J?=?7.2?Hz, H-3), 2.43 (1H, s, OH), 1.86 (2H, quin, J?=?7.6?Hz, H-2); 13C NMR (CDCl3, 100?MHz): delta 146.2 (C-1′), 132.8 (C-3′, 5′), 130.2 (C-2′, 6′), 126.8 (C-4′), 65.8 (C-1), 38.3 (C-2), 31.9 (C-3); LC-MS: m/z 135.2 (M?-?H)-.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103-25-3, its application will become more common.

Reference:
Article; Meka, Bharani; Ravada, Suryachandra Rao; Muthyala, Murali Krishna Kumar; Kurre, Purna Nagasree; Golakoti, Trimurtulu; Bioorganic Chemistry; vol. 80; (2018); p. 408 – 421;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 53518-15-3, name is 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 53518-15-3, SDS of cas: 53518-15-3

A vial was charged with S6 (20 mg, 0.027 mmol), 7-amino-4-(trifluoromethyl)coumarin (19 mg, 0.08 1 mmol, 3 eq.), HATU (31 mg, 0.081 mmol, 3 eq.), Et3N (76 1iL, 0.543 mmol, 20 eq.) and DIvIF (500 jiL). Contents were stirred at room temperature and ambient atmosphere for 24 h, after which the solvent was concentrated to dryness, and the crude product was purified via reverse phase HPLC (10-95% MeCN/H20, linear gradient, with constant 0.1% v/v TFA additive; 23 mm run, 42 mL/min flow, detection at 550 nm) to afford S7 (8 mg, 31%). LRMS (ESI) calcd for C46H40F3N30I2S2 [Mj 948.0, found 948.1

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HOWARD HUGHES MEDICAL INSTITUTE; LAVIS, Luke; JRADI, Fadi, M.; (109 pag.)WO2018/182811; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics