Category: esters-buliding-blocks

2905-69-3, name is Methyl 2,5-dichlorobenzoate, 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: Methyl 2,5-dichlorobenzoate

Add 19.1 g of 2,5-dichlorobenzoic acid (0.1 mol) and 120 ml of methanol to the reaction flask.Add a catalytic amount of acid and reflux at 65~70 C for 8 hours.After the reaction, the excess methanol was distilled off under reduced pressure.19.2 g of methyl 2,5-dichlorobenzoate was obtained in a yield of 93.6%.The obtained methyl 2,5-dichlorobenzoate (0.094 mol) was added to the reaction flask.Add 30 g of bromine (0.19 mol) and 2.5 g of aluminum tribromide.The reaction was carried out at 50 C for 6 hours, and after the reaction was completed, it was extracted with ethyl acetate and water.After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to give 24 g of Compound 3.The yield was 90.2%.Adding the obtained compound 3 to the reaction flask,Add 60 ml of methanol and a suitable palladium catalyst and react at 80 C for 6 hours.The reaction was extracted, dried, and the solvent was evaporated under reduced pressure to give 17.1 g of Compound 4.The yield was 86%.Finally, the compound 4 was placed in a reaction flask, 100 ml of deionized water was added, and an appropriate amount of acid was added, and the reaction was carried out at 60 C for 3 hours. After the reaction was completed, it was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The final product, dicamba, 14.5 g was obtained after pressure distillation.The total yield is 65%.

The synthetic route of 2905-69-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Changqing Agrochemical Co., Ltd.; Yu Guoquan; Sun Xialin; Ma Changqing; Ding Huaping; (6 pag.)CN109134232; (2019); A;,
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Related Products of 174403-69-1, 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. 174403-69-1, name is Methyl 4-fluoro-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of pyrazole (100 mg, 1.47 mmol), methyl 4-fluoro-2-methylbenzoate (123.51 mg, 0.73 mmol) and potassium carbonate (609.0 mg, 4.41 mmol) in N,N-dimethylformamide (5 mL) was stirred at 60 C for 16 h. The reaction was poured into water (5 mL) and extracted with EtOAc (20 mL). The organic extract was washed with water (20 mL x 2) and brine (10 mL), dried over Mg504 and concentrated. The residue was purified by prep-TLC (33% ethyl acetate in petroleum ether, Rf = 0.3) to afford methyl 2-methyl-4-(1H-pyrazol-1-yl)benzoate (50 mg, 15.7% yield) as a white solid. LCMS (Method 5-95AB): tR =0.732 mi [M + Hj = 216.9.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-fluoro-2-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; RQX PHARMACEUTICALS, INC.; GENENTECH, INC.; CHEN, Yongsheng; SMITH, Peter Andrew; ROBERTS, Tucker Curran; HIGUCHI, Robert I.; PARASELLI, Prasuna; KOEHLER, Michael F. T.; SCHWARZ, Jacob Bradley; CRAWFORD, James John; LY, Cuong Q.; HANAN, Emily J.; HU, Huiyong; YU, Zhiyong; (424 pag.)WO2017/84630; (2017); A1;,
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Reference of 53518-15-3, 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 53518-15-3 as follows.

The Schiff base was synthesized from the condensation reaction between 7-amino-4-(trifluoromethyl)coumarin (0.2684g; 1.171mmol) and 20 2-amino-3-formylchromone (0.2216g; 1.171mmol) in 16 methanol (20cm3) which was heated under reflux for 3h. The resultant yellow solution was allowed to cool to room temperature before the light yellow precipitate was filtered and washed using cold methanol and 21 petroleum ether. Yield=50%; Melting point: 239.9-244.8C; Infrared (vmax/cm-1): nu(N-H) 3242, 3093 (br), nu(C=O) 1679 (s), nu(C=N) 1610 (s), nu(C-O-C) 1334 (s); 1H NMR (d6-DMSO/298K/ppm): 10.09 (s, 1H, H11), 9.59 (s, 2H, NH2), 8.05-8.01 (dd, J=7.7Hz, J=1.7Hz, 1H, H15), 7.76-7.70 (t, J=1.5Hz, J=1.1Hz, 3H, H17), 7.48-7.33 (m, 3H, H8, H16, H18), 6.68-6.64 (dd, J=8.8Hz, J=2.2Hz, 1H, H9), 6.53-6.50 (d, J=2.2Hz, 1H, H6), 6.43 (s, 1H, H3); 13C NMR (d6-DMSO/295K/ppm): 188.42 (C13), 175.58 (C20), 165.96 (C4), 159.86 (C19), 157.05 (C2), 154.57 (C11), 153.60 (C5), 134.59 (C7), 126.22 (C9), 126.20 (C14), 125.83 (C16), 125.70 (C1), 122.70 (C17), 117.34 (C15), 112.69 (C18), 107.92 (C10), 107.86 (C8), 102.23 (C6), 99.46 (C3), 99.14 (C12); UV-Vis (Methanol, lambdamax (epsilon, M-1cm-1)): 377nm (1361), 292nm (1297), 264nm (1785), 234nm (2698); TOF-MS (m/z): Calcd: 400.0671, Found: 400.0753 [M]+, 401.0750 [M+H]+, 402.0785 [M+2H]+.

According to the analysis of related databases, 53518-15-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jadoo, Barushka; Booysen, Irvin Noel; Akerman, Matthew Piers; Rhyman, Lydia; Ramasami, Ponnadurai; Polyhedron; vol. 144; (2018); p. 107 – 118;,
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Adding a certain compound to certain chemical reactions, such as: 55666-43-8, name is tert-Butyl 3-bromopropanoate, 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 55666-43-8, Application In Synthesis of tert-Butyl 3-bromopropanoate

To a mixture of 2-sulfanyl-5,6,7,8-tetrahydro-4-quinazolinol (0.482 g, 2.64 mmol) and potassium carbonate (0.730 g, 5.29 mmol) in acetone was added tert-butyl 3-bromopropionate (0.663 g, 3.17 mmol). The mixture was stirred at 60C for 4 h (LC-MS indicated partial conversion to desired product). The solid was filtered off, and the solution was concentrated. The residual material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 0% to 50% EtOAc in hexane, to provide tert- butyl 3-((4-oxo-3,4,5,6,7,8-hexahydroquinazolin-2-yl)thio)propanoate (0.132 g, 0.425 mmol, 16.09 % yield) as white solid. lH NMR (400 MHz, DMSO-i/6) delta ppm 12.40 (br. s., 1 H) 3.24 (t, J=6.70 Hz, 2 H) 2.64 (t, J=6.75 Hz, 2 H) 2.42 – 2.49 (m, 2 H) 2.28 (br. s., 2 H) 1.60 – 1.78 (m, 4 H) 1.41 (s, 9 H). m/z (ESI) 31 1.2.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John L.; CHAKKA, Nagasree; DIMAURO, Erin F.; GUNAYDIN, Hakan; GUZMAN PEREZ, Angel; HUA, Zihao; HUANG, Xin; WO2014/36022; (2014); 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. 6279-86-3, name is Triethyl methanetricarboxylate, This compound has unique chemical properties. The synthetic route is as follows., 6279-86-3

1b) 6-Hydroxy-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone; A mixture of the compound from example 1(a) (0.342 g, 1.63 mmol), triethyl methanetricarboxylate (0.755 g, 3.25 mmol), methanolic sodium methoxide (0.378 mL of a 4.37 M solution, 1.65 mmol) and ethanol (3 mL) was stirred in a microwave reactor at 160 C. for 0.5 h, then cooled and poured into 1M aqueous hydrochloric acid (20 mL). The mixture was extracted with ethyl acetate, and the extracts washed with brine, dried (MgSO4) and evaporated under reduced pressure. The residue was chromatographed (silica gel, 5-10% methanol/dichloromethane) to give the title compound (0.320 g, 44%) as a foam. 1H NMR (400 MHz, DMSO-d6) delta ppm 5.05 (s, 2 H) 5.50 (s, 1 H) 6.87 (m, 2 H) 7.18-7.26 (m, 3 H) 7.36-7.43 (m,4H) 7.49 (m, 1 H) 11.64 (s, 1 H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Shaw, Antony N.; Duffy, Kevin J.; Tedesco, Rosanna; Wiggall, Kenneth; US2008/171756; (2008); A1;,
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Synthetic Route of 39503-58-7, These common heterocyclic compound, 39503-58-7, name is Methyl 5-bromo-2-methoxy-4-methylbenzoate, 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 solution of S2(12.8g, 48.8 mmol), N-bromosuccinimide (9.68 g, 54.78 mmol, 1.1 eq.), azobisisobutyronitrile (1.64 g, 9.96 mmol, 0.2 eq.) in carbon tetrachloride was heated at 70 C. After 14 h, solvent was removed and the residue purified by flash chromatography (Si02, 1 :9 ethyl acetate/hexanes) to afford S3 (13.92 g, 71.3 %) as a white amorphous solid. 1H NMR (500 MHz, CDC13) delta 7.91 (s, 1H), 7.60 (s, 1H), 7.00 (s, 1H), 3.99 (s, 3H), 3.90 (s, 3H).13C NMR (125 MHz, CDC13) delta 164.7, 159.0, 144.8, 135.5, 123.0, 114.6, 109.5, 56.7, 52.7, 39.3. HRMS (ESI+) m/z [M + H+] calcd for C10H11Br203, 336.9075, found 336.9079.

The synthetic route of 39503-58-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF KANSAS; BLAGG, Brian S. J.; KENT, Caitlin Nicole; MISHRA, Sanket Jaiprakash; (93 pag.)WO2018/132769; (2018); A1;,
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These common heterocyclic compound, 6279-86-3, name is Triethyl methanetricarboxylate, 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. Safety of Triethyl methanetricarboxylate

10129] 14.5 parts (62.4 mmol) of triethyl carboxymalonate,11.4 parts (76.4 mmol) of 5-amino-2-benzimidazolinone and0.138 part (0.626 mmol) of 2,6-di-tert-butyl-p-cresol weredissolved in 141 parts (1.93 mol) of N,N-dimethylformamide, and reacted under heating and stirring at 800 C. for 6hours. After the reaction, N,N-dimethylformamide was distilled away under reduced pressure, and 300 parts (16.7 mol) of water was added to the obtained residue. The deposit was filtered to thereby obtain the intermediate (4).

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

Reference:
Patent; CANON KABUSHIKI KAISHA; CANON FINETECH INC.; Kubo, Haruko; Ueno, Suzuka; Chizuwa, Junko; Yamamoto, Tomoya; Itabashi, Hitoshi; Terui, Yuhei; Yoshida, Yu; Murai, Yasuaki; Toyoda, Takayuki; (26 pag.)US2016/130233; (2016); A1;,
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These common heterocyclic compound, 108928-00-3, name is Ethyl 2,4-difluorobenzoate, 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. COA of Formula: C9H8F2O2

2,4-Difluorobenzoic acid ethyl ester (5.33g) was cooled to 0C and treated with concentrated sulfuric acid (3. 5mL) and then fuming nitric acid (3. 5mL). The mixture was stirred for 2 hours at 0C and then partitioned between dichloromethane (2x50mL) and water (25mL). The organic phase was back extracted with water (25mL) and then dried over magnesium sulfate and concentrated in vacuo. This provided the desired compound as a white solid (5. 00g) which was used without further purification.

The synthetic route of Ethyl 2,4-difluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM P.L.C.; WO2003/87098; (2003); 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. 1260092-46-3, name is tert-Butyl 3-(2-aminoethoxy)propanoate, A new synthetic method of this compound is introduced below., name: tert-Butyl 3-(2-aminoethoxy)propanoate

To a solution of fert-butyl 3-(2-aminoethoxy)propanoate (246 mg, 1.302 mmol) in DMF (1.5 ml) at rt was added bis(2,5-dioxopyrrolidin-l-yl) 3,3′-oxydipropanoate (232 mg, 0.651 mmol) and followed DIPEA (0.284 ml, 1.628 mmol). The mixture was allowed to stir at rt over night and concentrated to dryness. To the resulting residure at 0 C was added 1.0 mL neat TFA, and the resulting mixture was allowed to stir at rt overnight. The mixture was concentrated to give the crude product, which was used without further purification. UPLC-MS Method A: TR = 0.7 min, m/z = 393 (z = 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; MERCK SHARP & DOHME CORP.; LIN, Songnian; YAN, Lin; HUO, Pei; PISSARNITSKI, Dmitri; FENG, Danqing; NARGUND, Ravi; MADSEN-DUGGAN, Christina; ZHU, Yuping; KEKEC, Ahmet; WU, Zhicai; (191 pag.)WO2017/205309; (2017); A1;,
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Application of 921222-14-2, 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. 921222-14-2 name is Ethyl 2,3-diamino-6-(methylthio)benzoate, 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.

To a solution of 2,3-diamino-6-methylsulfanyl-benzoic acid ethyl ester (150 mg) in acetonitrile (10 mL) are added 2,3-dichlorophenyl isothiocyanate (98 muL). The reaction mixture obtained is stirred 1 hour at RT and N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydro-chloride (EDCI, 166 mg) is added. The mixture obtained is cooled to RT, quenched with H2O and extracted with EtOAc. The organic layers obtained are combined, dried over MgSO4, filtrated and solvent is evaporated to afford the title compound (LC/MS Rt=3.55, [M]+=395.93 and 397.89 and 399.89).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2,3-diamino-6-(methylthio)benzoate, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/9774; (2007); A1;,
Ester – Wikipedia,
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