Month: July 2021

Reference of 1678-68-8, These common heterocyclic compound, 1678-68-8, name is trans-Ethyl 4-aminocyclohexanecarboxylate, 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.

1-(2-Methanesulfonylpyrimidin-4-yl)-1H-indazole (6.4 g) was suspended in THF and the mixture heated to 60 C. until complete dissolution of the solids. trans-4-Amino-cyclohexane-carboxylic acid ethyl ester (7.99 g, 46.6 mmol) was added, followed by TEA (9.7 mL, 69.9 mmol), and the resulting mixture stirred overnight. The reaction mixture was concentrated under reduced pressure until solids started to precipitate, and was then heated to 60 C. for 24 h. THF (4 mL) was added, and the reaction mixture stirred for 64 h at 60 C. The resulting mixture was extracted with EtOAc, the combined organic extracts washed with water, dried over MgSO4, filtered, and evaporated under reduced pressure. The crude residue was purified by flash chromatography (DCM/MeOH, 98:2) and the brown solid obtained was triturated with Et2O to give trans-4-(4-indazol-1-ylpyrimidin-2-ylamino)-cyclohexanecarboxylic acid ethyl ester (2.883 g) as a white solid.

Statistics shows that trans-Ethyl 4-aminocyclohexanecarboxylate is playing an increasingly important role. we look forward to future research findings about 1678-68-8.

Reference:
Patent; Roche Palo Alto LLC; US2008/146565; (2008); 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. 3044-06-2, name is Diethyl 2-(1-ethoxyethylidene)malonate, A new synthetic method of this compound is introduced below., name: Diethyl 2-(1-ethoxyethylidene)malonate

4-isopropoxy-3-cyanobenzidine hydrochloride (1 g, 0.0042 mol), M-230 (1.06 g, 0.0046 mol),A fresh methanol solution of sodium ethoxide (3 g of sodium hydride (20%) was added to 100 ml of ethanol at a low temperature) (20 ml), and refluxed for 2 hours. After the reaction was completed by TLC, the reaction mixture was cooled to room temperature, and 6N was gradually added to the reaction mixture. ofThe pH of the mixture was adjusted to 1 with HCl, stirred for 30 min, filtered, filtered, washed with water and dried. The obtained crude product was recrystallized from ethanol to give a white solid, 0.44 g.Yield: 31.1%

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; Shenyang Hainuowei Pharmaceutical Technology Co., Ltd.; Wang Shaojie; Mao Qing; Zhang Bing; (30 pag.)CN110156698; (2019); 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. 2150-37-0, name is Methyl 3,5-dimethoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C10H12O4

Step 1: Intermediate 1 [00789j To a solution of methyl 3,5-dimethoxybenzoate (2.00 g, 10.2 mmol) in CH3CN (20 mL), 1 -(chloromethyl)-4-fluoro- 1 ,4-diazoniabicyclo [2.2 .2]octane ditetrafluoroborate (SelectfluorTM, 5.40 g, 15.2 mmol) was added. The reaction was stirred at room temperature overnight after which it was diluted with water and extracted with ethyl acetate. The organic layers were washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The resultant residue was purified by column chromatography (hexane/ethyl acetate: 10/1) to afford the title compound as white solid (800 mg, 38 %). ?H NMR (400 MHz, CDC13): oe 3.81 (s, 3H), 3.87 (s, 3H), 3.93 (s, 3H), 6.70 (dd, 1H), 6.91 (dd, 1H).

The synthetic route of 2150-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; SANOFI; D’AGOSTINO, Laura Akullian; SJIN, Robert Tjin Tham; NIU, Deqiang; MCDONALD, Joseph John; ZHU, Zhendong; LIU, Haibo; MAZDIYASNI, Hormoz; PETTER, Russell C.; SINGH, Juswinder; BARRAGUE, Matthieu; GROSS, Alexandre; MUNSON, Mark; HARVEY, Darren; SCHOLTE, Andrew; MANIAR, Sachin; WO2014/144737; (2014); A1;,
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Reference of 55666-43-8, These common heterocyclic compound, 55666-43-8, name is tert-Butyl 3-bromopropanoate, 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.

0.3 g of the molecule 5 was dissolved in 5 ml of dry DMF,Cold to 0 degrees,Adding 40 mg of sodium hydride,Reaction for 15 minutes,Adding one equivalent of t-butyl 3-bromopropionate,Reaction for half an hour, warming up to 50 degrees reaction 24 hours,Rotate DMF, add 20 ml of water,Ethyl acetate extraction, combined organic phase,Saturated with salt water, anhydrous sodium sulfate drying, pumping, spin drying, and then silica gel column to get the molecular 6, the yield of 45%

Statistics shows that tert-Butyl 3-bromopropanoate is playing an increasingly important role. we look forward to future research findings about 55666-43-8.

Reference:
Patent; University of Science and Technology of China; Zhang Guoqing; Chen Biao; Xu Cheng; Wang Hao; Du Jiajun; Bi Guoqiang; Luo Yi; (111 pag.)CN107118586; (2017); A;,
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Synthetic Route of 94994-25-9, These common heterocyclic compound, 94994-25-9, name is Methyl 4-formylbicyclo[2.2.2]octane-1-carboxylate, 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.

EXAMPLE 21 4-[4-Benzo[1,3]dioxol-5-yl-5-(6-methyl-pyridin-2-yl)-1H-imidazol-2-yl]-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester 4-Formyl-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester (0.284 g, 1.0 mmol) was added to a solution of 1-benzo[1,3]dioxol-5-yl-2-(6-methyl-pyridin-2-yl)-ethane-1,2-dione 2-oxime (see Example 4; 0.215 g, 1.1 mmol) and ammonium acetate (1.54 g, 20 mmol) in acetic acid (5 mL). The mixture was refluxed for 2 hours. Solvent was removed under reduced pressure. The reaction mixture was then quenched with ammonia/ice mixture. The aqueous solution was extracted with ethyl acetate. Ethyl acetate extract was washed with brine, dried over sodium sulfate, filtered, and concentrated to give 0.300 g (65%) of the hydroxyimidazole as a yellow solid. MS (ESP+) m/z 462.3 (M+1).

Statistics shows that Methyl 4-formylbicyclo[2.2.2]octane-1-carboxylate is playing an increasingly important role. we look forward to future research findings about 94994-25-9.

Reference:
Patent; Lee, Wen-Cherng; Sun, Lihong; Shan, Feng; Chuaqui, Claudio; Zheng, Zhongli; Petter, Russell C; US2006/63809; (2006); A1;,
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Reference 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diethyl 2-bromo-2-methylmalonate, its application will become more common.

Reference:
Article; Swift, Elizabeth C.; Williams, Theresa M.; Stephenson, Corey R. J.; Synlett; vol. 27; 5; (2016); p. 754 – 758;,
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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. 20372-66-1, name is Methyl 2,4,5-trifluorobenzoate, A new synthetic method of this compound is introduced below., Formula: C8H5F3O2

Methyl 2,4,5-trifluorobenzoate (DSL Chemicals, 950 mg, 5 mmol), sodium cyanide (306 mg, 6.25 mmol) and tetrabutylammonium bromide (2.01 g, 6.25 mmol) were dissolved in DMF (10 mL) and the resulting mixture was heated at 600C overnight. Additional amount of sodium cyanide (306 mg, 6.25 mmol) was added and the mixture was stirred at 600C for 24 additional hours. The reaction mixture was diluted with EtOAc and washed with brine several times. The organic layer was dried over MgSO4 and concentrated under vacuum. The residue was purified by flash chromatography (silica, EtOAc/cHex) to give the title compound. 1H NMR (DMSO-dbeta, 300 MHz) delta 7.77 (dd, J=8.4, 5.5 Hz, 1 H), 7.42 (dd, J=8.9, 5.0 Hz, 1 H), 3.96 (s, 3H). LC/MS (Method B): 463.2 (M-H)”, 465.2 (M+H)+. HPLC (Method A) Rt 3.63 min (Purity: 99.9%).

The synthetic route of 20372-66-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SERONO S.A.; QUATTROPANI, Anna; MONTAGNE, Cyril; SAUER, Wolfgang; CROSIGNANI, Stefano; BOMBRUN, Agnes; WO2010/112461; (2010); 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. 35179-98-7, name is Chloromethyl ethyl carbonate, A new synthetic method of this compound is introduced below., SDS of cas: 35179-98-7

Sodium IODIDE (25 MG) was dissolved in acetonitrile (0. 15 mL) in which had been dissolved chloromethyl ethyl carbonate (22 mg) [Z. Li et al. , Bioorg. Med. CHEM. LETT., 7,2909 (1997)], and the solution was stirred for four hours under dark room conditions at room temperature. Next, the solution was added to DMF (0. 30 mL) in which had been dissolved BOC–ALA-HIS (TRT) (30 mg) and DIISOPROPYLETHYLAMINE (0. 019 ML), and stirring was further carried out for 3 days at room temperature. After that, ethyl acetate (30 mL) was added to the solution obtained, and the solution was washed with a sodium hydrogencarbonate aqueous solution (5 mL) twice and a sodium chloride aqueous solution (5 ML) once. After the washing, drying was carried out with sodium sulfate, concentration was carried out under reduced pressure, the concentrate was dissolved in a mixed liquid of acetonitrile and water (1: 4), and then freeze drying was carried out, thus obtaining A white powder (approximately 55 mg). The powder was treated for 30 minutes with TFA (1.2 ML) CONTAINING 2% TRIISOPROYLSILANE and 2% water, and then washing was carried out three times with ether (10 mL). The residue was dissolved in a mixed solution of acetonitrile and water (1: 4), and then freeze drying was carried out, thus obtaining 28 mg of crude product. The crude product obtained was subjected to HPLC (with an ODS column) with the undermentioned conditions using water- acetonitrile containing 0. 1T TFA as an eluent, the fraction containing THE TARQET COMPOUND (ss-ALA-HIS-OCH2-OCO-OCH2CH3) was isolated using the absorbance at 220 nm as an indicator, and freeze drying was carried out, thus obtaining a white powder (19 mg) of P-ALA-HIS-OCH2-OCO-OCH2CH3 (TFA salt). This powder was dissolved in a 0. 05 M HC1 aqueous solution containing 5% acetonitrile, and freeze drying was again carried out, whereby the target compound (-ALA-HIS-OCH2-OCO-OCH2CH3 2HC1) WAS obtained as a white powder (11 mg, 52T yield). LT;HPLC CONDITIONS GT; Column : Cosmosil 5C18-MS 10 x 250 mm Eluent : Solution A: Water containing 0. 1% TFA Solution B: Acetonitrile containing 0. 1% TFA Concentration gradient Time (min) 0 20 25 Solution B % 5 15 95 Flow rate : 2.5 ML/MIN -H NMR (400 MHz, DMSO-d6, 25C) : No. 1. 23 (3H, t, J = 7.1 Hz), 2.46-2. 58 (2H, m), 2. 88-2. 98 (2H, m), 3.07 (1H, dd, J = 8.8 and 15.1 Hz), 3.16 (1H, dd, J = 5.7 and 15. 1 Hz), 4.19 (2H, q, J = 7.1 Hz), 4.58-4. 66 (1H, m), 5.69 (1H, d, J = 6.1 Hz), 5.72 (1H, d, J = 6. 1 HZ), 7.44 (1H, s), 7. 87 (3H, br), 8.87 (1H, d, J = 7.2 Hz), 9. 01 (1H, S), 14.35 (2H, br) ; DUC NOR (100 MHz, DMSO-DS, 25C) : 8 13.9, 25. 6,31. 8,34. 9, 51.3, 64.5, 82.4, 117. 2, 128.6, 133.9, 153.1, 169. 3, 169. 8; ESI-MS: m/z 329 (M+H) ; calculated for CL3H2LN406 : 329.

The synthetic route of 35179-98-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OSAKA INDUSTRIAL PROMOTION ORGANIZATION; OSAKA UNIVERSITY; WO2005/9471; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 344-14-9,Some common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, molecular formula is C5H7FO4, 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: [Pd(C3H5)Cl]2 (0.004 mmol, 4 mol%), [6-(allyloxymethyl)-N-(2-((R)-((S)-1-(3,5-dimethoxyphenyl)propyl)sulfinyl)phenyl)picoli-namide] (6b, 0.008 mmol, 8 mol%), and (E)-1,3-disubstituted allyl acetates 7 (0.1 mmol) were dissolved in THF (2.0 mL) in a dry Schlenk tube filled with argon. The reaction mixture was stirred for 30 min at room temperature. Then Cs2CO3 (3.0 equiv) and dimethyl 2-fluoromalonate 8 (0.3 mmol, 3.0 equiv) were added. After the completion of the reaction monitoring by TLC, the crude reaction mixture was filtrated with celite and the solvent was removed under reduced pressure. The crude residue was purified by flash column chromatography (petroleum ether/ethyl acetate) to give the desired products 9.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl 2-fluoromalonate, its application will become more common.

Reference:
Article; Zhang, Min; Zhao, Mingzhu; Zheng, Purui; Zhang, Hongbo; Zhao, Xiaoming; Journal of Fluorine Chemistry; vol. 189; (2016); p. 13 – 21;,
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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. 25662-28-6, name is Methyl 1-cyclopentene-1-carboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C7H10O2

EXAMPLE 20 2-(Piperidin-4-ylsulfanyl)cyclopentanecarboxylic acid methyl ester methyl 1-cyclopentene-1-carboxylate (0.24 ml) and Intermediate 12 (0.50 g) were dissolved in anhydrous methanol (20 ml), degassed with nitrogen, and cooled to -10 to -15 C. sodium bis(trimethylsilyl)amide, 1.0 M in tetrahydrofuran (1.93 ml) was added and the reaction stirred for 18 h, warming to room temperature.The reaction mixture was then evaporated and the residue partitioned between ethyl acetate (20 ml) and water (20 ml).The aqueous was extracted once more with ethyl acetate (10 ml) and the combined organic extracts were washed with 2% aqueous citric acid (20 ml), water (20 ml), saturated sodium bicarbonate (20 ml), saturated brine (20 ml), dried (Na2SO4) and evaporated under reduced pressure. The resultant amber oil was dissolved in dichloromethane (10 ml) and treated with trifluoroacetic acid (2 ml).After stirring at room temperature for 17 h, the solvents were evaporated and the residue azeotroped with 1:1 dichloromethane/hexane (3*20 ml).The residue was then dissolved in water (30 ml) and washed with diethyl ether (2*10 ml) before being basified with sodium carbonate to PH 11 and extracted with ethyl acetate (4*15 ml).The combined ethyl acetate extracts were then washed with saturated brine (10 ml), dried (Na2SO4) and reduced in vacuo to provide the title compound as a colourless gum (0.15 g, 31%). TLC Rf 0.26 (6% methanol/dichloromethane containing a trace of aqueous ammonia) MS 244 (MH+)

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; Montana, John Gary; Baxter, Andrew Douglas; Owen, David Alan; Watson, Robert John; US2003/236416; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics