Tag: M.W=100-200

Application of 403-33-8, A common heterocyclic compound, 403-33-8, name is Methyl 4-fluorobenzoate, molecular formula is C8H7FO2, 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.

General procedure: 4-fluorobenzoic acid as the raw material, methanol as a reaction solvent, a small amount of concentrated sulfuric acid catalyst, followed by stirring under heating at reflux, thin layer chromatography (TLC) to track progress of the reaction, a certain amount after the completion of the reaction NaHCO3Solution for hydrazine and the reaction liquid solution to give ester intermediate (3-1), continue to add more than the corresponding proportion of hydrazine hydrate reaction mixture was heated with stirring at reflux, thin layer chromatography (TLC) to track progress of the reaction, the reaction after completion of the reaction solution was added to a certain amount of water, then a large amount of white sink to the bottom, suction filtration to afford intermediate hydrazides (3-2)

The synthetic route of 403-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan People Hospital; Shi Jianyou; (21 pag.)CN106957242; (2017); A;,
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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. 46193-76-4, name is Ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate, A new synthetic method of this compound is introduced below., Quality Control of Ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate

Ethyl-6-nitro-4H-thieno[3,2-b]pyrrole-5-carboxyIate (95). Pulverized Cu(NO3)2′ hydrate (953 mg, 4.10 mmol) dissolved in acetic anhydride (8.2 niL) was added dropwise to a solution of carboxylate 96 dissolved in acetic anhydride (10 mL) at 0 0C. The addition was completed in 1.5 h and the mixture was then stirred at r.t. for 2 h. After filtration the organic layer was poured over ice and extracted with diethyl ether (3×30 mL). The combined organic layers were washed with saturated aqueous sodium carbonate solution and dried over MgSO4. After the removal of organic solvent, the residue was purified by column chromatography (EtOAc/Hexane: 1/6) to give the desired nitration product 94 (148 mg, 12 %) as a light yellow solid along with another nitration product 95 (300 mg, 25%).

The synthetic route of 46193-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; THOMAS, Craig J.; AULD, Douglas S.; INGLESE, James; SKOUMBOURDIS, Amanda P.; JIANG, Jian-Kang; BOXER, Matthew; WO2010/42867; (2010); A2;,
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Application of 4606-07-9,Some common heterocyclic compound, 4606-07-9, name is Ethyl cyclopropanecarboxylate, molecular formula is C6H10O2, 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 10 3-(5-Cyclopropyl-1,2,4-oxadiazol-3-yl)-6-methoxy-5-morpholino-imidazo[1,5-a]quinazoline (Compound 70) A mixture of 6-methoxy-5-morpholino-imidazo[1,5-a]quinazoline-3-carboxamide oxime (0.9 g), ethyl cyclopropylcarboxylate (1.7 g), molecular sieves (3 g), and 80% sodium hydride (0.1 g) in 20 ml of dry DMF was heated for 11/2 hours at 120 C. The mixture was cooled to room temperature, diluted with acetic acid (0.5 ml) and methylene chloride (20 ml) and filtered. The filtered mixture was evaporated and the residue was purified by column chromatography (HPLC) (eluent: methylene chloride:acetone (2:1)) to give yellow crystals of the title compound, m.p. 227-228 C. Yield 0.38 g. In the same manner the following compound was prepared:

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

Reference:
Patent; Novo Nordisk A/S; US5371080; (1994); A;,
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Synthetic Route of 758684-29-6, A common heterocyclic compound, 758684-29-6, name is Methyl 3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylate, molecular formula is C10H11NO3, 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.

4-Methoxybenzaldehyde (31.5 mu,, 0.259 mmol) and acetic acid (50 0.873 mmol) were added to a solution of methyl 3,4-dihydro-2H-benzo[b][l,4]oxazine-6-carboxylate (50.0 mg, 0.259 mmol) in 1,2-dichloroethane (2 mL), and the reaction mixture was placed on a heater/shaker at 50 C for 2 hours. Sodium triacetoxyborohydride (137 mg, 0.647 mmol) was added, and the reaction was placed on the heater/shaker at 50 C overnight. The reaction was diluted with dichloromethane, washed with brine, and passed through an Isolute phase separator. The filtrate was concentrated and purified by column chromatography on silica gel (Biotage 10 gram column, eluting with 10-60% ethyl acetate-hexanes) to afford methyl 4-(4- methoxybenzyl)-3,4-dihydro-2H-benzo[b][l,4]oxazine-6-carboxylate which was used directly in the next step MS: (ES, m/z): 314 [M+H]+.

The synthetic route of 758684-29-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; NG, Pui, Yee; THOMASON, Jennifer, R.; ZABLOCKI, Mary-Margaret; HAN, Bingsong; BARCZAK, Nicholas; LIU, Cuixian; RUDNITSKAYA, Aleksandra; LANCIA JR., David, R.; BAIR, Kenneth, W.; (315 pag.)WO2017/40963; (2017); A1;,
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Synthetic Route of 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.

To a stirred solution of 3-butyl-3-ethyl-8-hydroxy-2-methyl-7-(methylthio)-5-phenyl-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine 1,1-dioxide (Intermediate 152; 200 mg, 0.46 mmol) in dry THF (3 mL), DABCO (5.10 mg, 0.05 mmol) and tert butyl propiolate (0.1 mL, 0.7 mmol) were added at room temperature, and the reaction mixture was stirred for 1 hour at room temperature. After completion of the reaction (monitored by LCMS), the reaction mixture was diluted with ice-cold water (10 mL). The aqueous layer was extracted with EtOAc (2¡Á10 mL). The combined organic layer was dried over anhydrous Na2SO4 and evaporated under vacuum. The resulting crude material was purified by Isolera column chromatography (eluent: 6% EtOAc in hexane; silica gel: 230-400 mesh) to afford the title compound. Yield: 75% (190 mg, white solid). H NMR (400 MHz, DMSO-d6): delta 7.61 (d, J=12.4 Hz, 1H), 7.38 (t, J=8.0 Hz, 3H), 7.30 (d, J=7.6 Hz, 2H), 7.12 (t, J=7.2 Hz, 1H), 6.46 (s, 1H), 5.31 (d, J=12.4 Hz, 1H), 4.12 (s, 2H), 2.88 (s, 3H), 2.08 (s, 3H), 1.92-1.86 (m, 1H), 1.82-1.76 (m, 1H), 1.55-1.43 (m, 10H), 1.19-1.08 (m, 5H), 0.83-0.62 (m, 6H). LCMS: (Method A) 505.2 (M+-tBu+H), Rt. 3.65 min, 97.40%.

The synthetic route of 13831-03-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Albireo AB; Gillberg, Per-Goeran; Mattsson, Jan; Starke, Ingemar; Kulkarni, Santosh S.; (152 pag.)US2019/367467; (2019); A1;,
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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. 56741-34-5, name is Methyl 5-amino-2-fluorobenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 5-amino-2-fluorobenzoate

General procedure: To a solution of 11a (500 mg, 1.85 mmol) in acetone (10 mL) was added 12 (380 mg, 1.85 mmol) and pyridine (0.45 mL, 5.54 mmol).The mixture was stirred at 55 C for 1 h. The mixture was concentrated,diluted with ethyl acetate and washed with 1M HCl and brine twice.Then, the ethyl acetate layer was dried over anhydrous sodium sulfate andconcentrated to give the crude product. The crude product was purified bysilica column eluting with petroleum ether/ethyl acetate (5/1-2/1) to givethe desired product (0.33 g, yield 44.3%) as grey solid

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:
Article; He, Yulong; Dou, Huixia; Gao, Dingding; Wang, Ting; Zhang, Mingming; Wang, Heyao; Li, Yingxia; Bioorganic and Medicinal Chemistry; vol. 27; 19; (2019);,
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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. 35598-05-1, name is Methyl 4-methoxy-2-methylbenzoate, A new synthetic method of this compound is introduced below., COA of Formula: C10H12O3

2-Bromomethyl-4-methoxy-benzoic acid methyl esterTo a solution of 4-Methoxy-2-methyl-benzoic acid methyl ester (6.92g, 38.4 mmol) in CCI4 (100 mL) was added N-bromosuccinimide (7.99 g, 1.17 mmol). Benzoyl peroxide (1.82 g, 7.54 mmol) was added to the slurry and the mixture was heated at reflux for 18 h. The reaction was cooled and the solid was filtered off. The filtrate was absorbed onto silica to perform chromatography (0-10 % ethyl acetate/hexanes) to yield 2-Bromomethyl-4-methoxy- benzoic acid methyl ester, (6.12 g, 62 %, CASNo. 15365-25-0). MS: ES M+1 : 258.9, M+2 260.9 (258.0, 260.0).

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; PFIZER PRODUCTS INC.; WO2008/20306; (2008); A2;,
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Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 66315-16-0, name is Methyl 3-amino-4-(methylamino)benzoate, 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 66315-16-0, Application In Synthesis of Methyl 3-amino-4-(methylamino)benzoate

Intermediate 43: 2-Cyclopentylmethyl-l -methyl- 1 H-benzoimidazo le-5 -carboxylic acid 43.1 : 3-(2-Cyclopentyl-acetylamino)-4-methylamino-benzoic acid methyl ester 650 mg (5.07 mmol) cyclopentyl-acetic acid was stirred with 1.80 g (5.61 mmol) TBTU and 2.00 mL (14.4 mmol) TEA in 50 mL DMF at RT. After 30 min, 900 mg (5.00 mmol) 3-amino-4- methylamino-benzoic acid methyl ester was added and the mixture was stirred at RT for 3 h and at 50 C for 12h. The solvent was removed by distillation. The residue was taken up in aqueous potassium carbonate solution and water and extracted with EtOAc. The combined organic extracts were washed with water and saturated brine, dried over sodium sulfate, filtered and concentrated in vacuo. yield: 1.10 g (76 %) ESI-MS: m/z = 291 (M+H)+ Ri(TLC): 0.23 (DCM/MeOH = 19: 1)

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Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HEIMANN, Annekatrin; DAHMANN, Georg; GRUNDL, Marc; MUELLER, Stephan Georg; WELLENZOHN, Bernd; WO2013/87805; (2013); A1;,
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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. 5335-05-7, name is Chloromethyl benzoate, A new synthetic method of this compound is introduced below., Safety of Chloromethyl benzoate

General procedure: To a solution of Compound 54B (150 mg, 0.24 mmol) in DMF (10 mL) was added chloromethyl isobutyrate (36 mg, 0.24 mmol) and Na2CO3 (50 mg, 0.48 mmol). The reaction mixture was stirred at 50 C for 3 hour. After cooling down to room temperature, the mixture was diluted with water (50 mL) and extracted with ethyl acetate (20 mL x 3). The combined extracts were washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to furnish Compound 54C. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used.

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; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
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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. 685-88-1, name is Diethyl fluoromalonate, A new synthetic method of this compound is introduced below., Safety of Diethyl fluoromalonate

Part A: A mixture of sodium metal (1.55 g, 67.4 mmol) and EtOH (15.0 mL, 257 mmol) was stirred at RT until nearly all sodium had reacted. Diethyl fluoromalonate (3.54 mL, 22.4 mmol) was added followed by acetamidine hydrochloride (2.14 g, 22.7 mmol). The reaction mixture was heated at reflux for 3 h, cooled to RT and concentrated under reduced pressure. The residue was diluted with water (ca. 50 mL) and acidified (pH=2) with 6M aqueous HCl, and the mixture was stirred at RT for 1 h as a precipitate formed. The solids were collected by suction filtration and washed with water. Excess solvent was removed in vacuo to give 4,6-dihydroxy-5-fluoro-2-methylpyrimidine (2.08 g, 64%) as a light gray solid. LCMS (m/z): 145 (M+H)+

The synthetic route of 685-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ICAGEN, INC.; US2007/197523; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics