Tag: M.W=100-200

35180-01-9, Adding a certain compound to certain chemical reactions, such as: 35180-01-9, name is Chloromethyl isopropyl carbonate, 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 35180-01-9.

41.4 g of Tenofovir monohydrate (commercially available or prepared as disclosed in CN1264387A) was added to 164 g of N-methylpyrrolidone at 20~25 C.,Then added under stirring triethylamine 40g, 20 ~ 25 C under stirring for 0.5 hours,Chloromethyl isopropyl carbonate was added 100g, warmed to 55-65 C incubated for 5 hours;Stop heating, cooling to 20 ~ 30 C, adding ethyl acetate 320g, purified water 180g,0 ~ 5 C under stirring after the separation, the lower layer and then 110g of ethyl acetate at 0 ~ 5 C under extraction,Combined ethyl acetate layer, purified water 0 ~ 5 C washed twice, each 320g,30 ~ 35 C concentrated ethyl acetate; cyclohexane was added to the concentrate 150mL,20 ~ 25 C under stirring for 10 hours, filtered, cyclohexane 20mL rinse,Tenofovir disoproxil, white solid.

According to the analysis of related databases, 35180-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Pan Xusong; Xiao Ning; Wang Yong; Xiang Zhixiang; Lu Chongyu; Jia Xiaoman; Luo Jie; Zheng Wei; (74 pag.)CN103626803; (2017); B;,
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18595-18-1, The chemical industry reduces the impact on the environment during synthesis 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, I believe this compound will play a more active role in future production and life.

j00646j A solution of methyl 3-amino-4-methylbenzoate (25 g, 151 mmol) in ethanol (62 mL) was charged with 70% conc. HNO3 (9.5 g, 151 mmol) and solution of cyanamide (9.5 g, 227 mmol) in water (25 mL) at room temperature. The resulting solution was heated to 90Cfor 16 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL) and stirred for 30 mm. The solid precipitated out was filtered, washed with ethyl acetate:diethyl ether and dried to give 28.6 g, 70% yield of the title compound as yellow solid. ?H NMR (400 MHz, DMSO-d6): oe = 9.33 (br. s, 1 H), 7.87 (dd, J= 7.94, 1.32 Hz, 1 H), 7.75 (d, J = 1.32 Hz, 1 H), 7.51 (d, J= 8.38 Hz, 1 H), 7.30 (s, 4 H), 3.86 (s, 3 H), 2.28 (s, 3 H); MS (ESj:m/z = 208.15 [M+H], 249 [M+ACN] LCMS: tR = 0.71, 0.79 mm.

The chemical industry reduces the impact on the environment during synthesis Methyl 3-amino-4-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; COFERON, INC.; FOREMAN, Kenneth, W.; JIN, Meizhong; WANNER, Jutta; WERNER, Douglas, S.; WO2015/106292; (2015); A1;,
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105-53-3, A common compound: 105-53-3, name is Diethyl malonate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

EXAMPLE 28 The following experiment demonstrates the in situ preparation of the onium compound in the process. In a reaction flask were added 137.5 g (1.1 mol) trans 1,4-dichlorobutene-2, 160.0 g (1.0 mol) diethyl malonate, 600 cc methylene chloride and 6.8 g (5 mol % based on diethyl malonate) N,N-dimethylbenzylamine. The mixture was stirred at ambient temperature for 20 minutes and 124.8 g (2.0 mol) flaked 90% potassium hydroxide then added in small portions over a one-hour period while maintaining the reaction temperature at 25 C. with external cooling. The reaction was then stirred at ambient temperature for four hours. Diethyl 2-vinylcyclopropane-1,1-dicarboxylate (126.6 g; 59.8% yield) was obtained.

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, Diethyl malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Emery Industries, Inc.; US4252739; (1981); A;,
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A common compound: 61644-18-6, name is Chloromethyl isobutyrate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 61644-18-6

At room temperature,N-(3-(5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)-propane-1-sulfonamide (0.1g, 0.2mmol)And triethylamine (57 muL, 0.40 mmol) was dissolved in DMF (1 mL).And add to it Chloromethyl isobutyrate(34 mg, 0.25 mmol).The reaction mixture was stirred at room temperature for 16 hr and then evaporated.The residue was purified by silica gel column chromatography ( petroleum ether / ethyl acetate (v/v) = 4/1 to 3/1).The title compound was obtained as a white solid (45 mg,37.5%).

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, 61644-18-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Tingjin; Tang Yin; Sun Mingming; Wang Qian; (74 pag.)CN103626765; (2016); B;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, A new synthetic method of this compound is introduced below., 25597-16-4

An Alternative Preparation of ethyl 3-(pyridin-2-yl)-4-(trifluoromethyl)isoxazole-5- carboxylate (IB); 1-B-l. Ethyl 2,3 -dibromo-4,4,4-trifluorobutanoate: Br 1 ,COOEtBr (1-B-l)[00110] Bromine (18.4 mL, 357 mmol) was added dropwise over 30 minutes to a solution of (E)-ethyl 4,4,4-trifluorobut-2-enoate (50 g, 297 mmol) in carbon tetrachloride (50 mL) at room temperature under nitrogen. The resulting dark red solution was refluxed for 4 hours. Additional bromine (2ml) was added and heating was continued until the HPLC analysis showed that the starting material had been consumed. The reaction mixture was concentrated under reduced pressure to give light brown oil which used in the next step without purification. HPLC (XBridge 5mu Cl 8 4.6×50 mm, 4 mL/min, Solvent A: 10 % MeOH/water with 0.2 % H3PO4, Solvent B: 90 % MeOH/water with 0.2 % H3PO4, gradient with 0-100 % B over 4 minutes): 2.96 and 3.19 minutes.

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; BRISTOL-MYERS SQUIBB COMPANY; PITTS, William, J.; DYCKMAN, Alaric, J.; SPERGEL, Steven, H.; WATTERSON, Scott, Hunter; WO2010/85582; (2010); A1;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 87-24-1, name is Ethyl 2-methylbenzoate, 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 87-24-1, 87-24-1

General procedure: In a glove box, add a ruthenium complex Ia (0.3 to 0.7 mg, 0.0002 to 0.001 mmol) to a 300 mL autoclave,Potassium methoxide (35-700 mg, 0.5-10 mmol), tetrahydrofuran (4-60 mL), and ester compounds (10-200 mmol).After sealing the autoclave, take it out of the glove box and fill it with 50 100atm of hydrogen.The reaction kettle was heated and stirred in an oil bath at 100 C for 10 to 336 hours.After the reaction kettle was cooled in an ice-water bath for 1.5 hours, the excess hydrogen was slowly released.The solvent was removed from the reaction solution under reduced pressure, and the residue was purified with a short silica gel column to obtain an alcohol compound. The results are shown in Table 5.

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, Ethyl 2-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang Zhongke Chuangyue Pharmaceutical Co., Ltd.; Ding Kuiling; Tang Yitian; Han Zhaobin; (55 pag.)CN110357923; (2019); A;,
Ester – Wikipedia,
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Some common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, molecular formula is C5H10O4, 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. 89-91-8

To a solution of methyl 2,2-dimethoxyacetate (8.7 g, 64.9 mmol, 7.98 mL, 1 eq) in dioxane (50 mL) and H20 (50 mL) was added LiOH H20 (3.27 g, 77.8 mmol, 1.2 eq) at 0 C . After addition, the mixture was stirred at this temperature for 1 h, and then the resulting mixture was stirred at 20C for 10 h. TLC indicated that one new spot formed. The reaction mixture was diluted with NaOH aqueous solution (1 M, 80 mL), and extracted with petroleum ether (80 mL x 3). The combined aqueous layers were acidified with HC1 (6 M) aqueous solution to pH=l, and then extracted with ethyl acetate (80 mL for 3 times). The combined organic layers were dried over Na2S04, filtered and concentrated under reduced pressure to give 3.54 g of a colorless oil, which was used directly in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 89-91-8, its application will become more common.

Reference:
Patent; SIGILON THERAPEUTICS, INC.; VEISEH, Omid; HEIDEBRECHT, Richard; WOTTON, Paul, Kevin; OBERLI, Matthias; MILLER, Robert, James; (498 pag.)WO2018/67615; (2018); A1;,
Ester – Wikipedia,
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A common compound: 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 61367-07-5

Example 14 4-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid methyl ester 1-(2-Chloro-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indole (300 g), 4-amino-cyclohexanecarboxylic acid ethyl ester HCl salt (155 g), and K2CO3(170 g) in NMP (2.35 L) were stirred at 80 C. for 5 h and then stirred overnight at room temperature. The reaction mixture was then stirred on an ice bath, and 2.5 L water was slowly added while stirring, and cooling continued until completion of the exothermic reaction. Upon cooling, the mixture was filtered, and resulting solid was rinsed with H2O and dried in vacuo overnight to yield 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid methyl ester (97%).

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, 61367-07-5, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Arzeno, Humberto Bartolome; Filonova, Lubov K.; Goldstein, David Michael; Gong, Leyi; Loe, Bradley E.; O’Brien, Erin M.; Palmer, Wylie Solang; Rotstein, David Mark; Silva, Tania M.; Tan, Yun-Chou; US2011/301171; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 4606-07-9, name is Ethyl cyclopropanecarboxylate, A new synthetic method of this compound is introduced below., 4606-07-9

(a) Bis(4-methoxyphenyl)cyclopropylcarbinol: The Grignard reagent was prepared from 12.7 g (0.53 mol) of magnesium filings and 93.5 g (0.50 mol) of 4-bromoanisole in 160 ml of absolute ether. 26.0 g (0.228 mol) of ethyl cyclopropanecarboxylate were slowly added dropwise to this solution and the mixture was then heated at the reflux temperature for 2.5 hours. The reaction solution was poured onto ice and diluted with about 300 ml of saturated ammonium chloride solution, so that the resulting precipitate dissolved. The solution was then extracted with ether and the ethereal phase was washed with water, dried and concentrated. Vacuum distillation of the crude product gave 39.2 g of a fraction at 195-200 C./0.18 mm Hg.

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; Hoechst Aktiengesellschaft; US4918073; (1990); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

13831-03-3,Some common heterocyclic compound, 13831-03-3, name is tert-Butyl propiolate, molecular formula is C7H10O2, 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.

Example 9 Methyl (E)-3-[[1-(pyridin-3-yl)naphthalen-2-yl]oxy]acrylate 1-(Pyridin-3-yl)naphthalen-2-ol (80 mg, 0.26 mmol) obtained in Example 8 (1) was dissolved in dimethylformamide (2 mL), sodium hydride (16 mg, 0.4 mmol) was added thereto in an ice bath, and the solution was stirred at room temperature. After 10 minutes, methyl propiolate (91 muL, 1.1 mmol) was added to the reaction solution and the reaction solution was further stirred at 110 C. After 16 hours, water was added to the reaction solution in an ice bath, extraction was carried out using chloroform, the organic layer was dried over sodium sulfate and filtered, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate_hexane=1:2) to obtain a crude material of methyl (E)-3-[[1-(pyridin-3-yl)naphthalen-2-yl]oxy]acrylate (25 mg, yield of 22%) and methyl (Z)-3-[[1-(pyridin-3-yl)naphthalen-2-yl]oxy]acrylate. j0682] A title compound (white crystal, 24 mg, yield of41%) was obtained according to the same method as inExample 9 using 4-(2-mercaptonaphthalen- 1 -yl)benzonitrile(40 mg, 0.15 mmol) obtained in Example 48 (3) and t-butylpropiolate (63 pL, 0.46 mmol).10683] ?H NMR (CDC13, 400 MHz): oe=1.43 (s, 9H), 5.46(d, 1H, J=15 Hz), 7.32 (d, 1H, J=8 Hz), 7.4-7.5 (m, 3H),7.5-7.6 (m, 2H), 7.63 (d, 1H, J=8 Hz), 7.78 (d, 2H, J=8 Hz),7.9-8.0 (m, 2H).

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

Reference:
Patent; J-Pharma Co., Ltd.; Endo, Tsuyoshi; Kobayashi, Kunio; Tanaka, Hiroto; Saito, Daisuke; Hirano, Masaharu; Endou, Hitoshi; Anzai, Naohiko; (68 pag.)US2017/290795; (2017); A1;,
Ester – Wikipedia,
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