Month: March 2021

Some common heterocyclic compound, 17641-08-6, name is 2-Chloro-N-(3-methoxyphenyl)acetamide, molecular formula is C9H10ClNO2, 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. HPLC of Formula: C9H10ClNO2

General procedure: A mixture of 2-chloro-N-(4-chlorobenzyl)acetamide 3a (0.22 g, 1.0 mmol), 4-hydroxy-N-phenethyl-benzenesulfonamide 7a (0.42 g, 1.5 mmol), K2CO3 (0.21 g, 1.5 mmol) and KI (33 mg, 0.2 mmol) in acetone (20 ml) was stirred at 60 C for 7.0 h. After the organic solvent was evaporated, the residual was diluted with water (20 ml), extracted with dichloromethane, washed with brine and then dried over Na2SO4. After filtration and condensation, the crude product was obtained and recrystallized in ethyl acetate/hexane (1:1, v: v) to afford 1a as white solid (0.19 g, yield 42%). SAPA 1v was prepared by the reaction of 2-chloro-N-(3-methoxyphenyl)acetamide 3q with 7a according to the procedure described for SAPA 1a. Yield 46%; mp 107.0-108.0 C. ESI-MS m/z 441.3 (M+H)+. HRMS (ESI) of C23H24N2O5S (M+H)+ calcd, 441.1479; found, 441.1479. 1H NMR (400 MHz, DMSO-d6) delta 10.13 (s, 1H), 7.71 (d, J = 8.7 Hz, 2H), 7.57 (s, 1H), 7.30 (s, 1H), 7.28-7.10 (m, 9H), 6.65 (d, J = 7.9 Hz, 1H), 4.79 (s, 2H), 3.70 (s, 3H), 2.91 (s, 2H), 2.65 (t, J = 7.5 Hz, 2H). 13C NMR (151 MHz, DMSO-d6) delta 166.4, 161.1, 160.0, 140.0, 139.2, 133.2, 130.1, 129.1, 128.8, 126.7, 115.5, 112.4, 109.7, 105.9, 67.5, 55.5, 44.6, 35.7. HPLC purity: tR = 8.100, 98.9%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17641-08-6, its application will become more common.

Reference:
Article; Li, Ya-Li; Qi, Xiang-Yu; Jiang, Hui; Deng, Xiao-Dong; Dong, Yan-Ping; Ding, Ting-Bo; Zhou, Lu; Men, Peng; Chu, Yong; Wang, Ren-Xiao; Jiang, Xian-Cheng; Ye, De-Yong; Bioorganic and Medicinal Chemistry; vol. 23; 18; (2015); p. 6173 – 6184;,
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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. 162787-61-3, name is 2-(Methylsulfonamido)benzoic acid, A new synthetic method of this compound is introduced below., SDS of cas: 162787-61-3

O-Benzoic acid methanesulfonamide (0.060g, 0.28 mmol), HATU(0.213g, 0.56 mmol), and pyridine(68ul, 0.84 mmol), were dissolved in anhydrous DMF (8 ml). The reaction was stirred under nitrogen for 2 hours to activate the acid. When activation was approximately 80% complete by LC/MS (2 hr) the piperidine intermediate 28 (0.073g, 0.28 mmol), along with DIPEA (96ul, 0.56mmol) were added dissolved in DMF(4 ml). The reaction was stirred overnight while monitoring by LC/MS. Solvents were removed by rotary evaporation. The residue was taken up in DCM (100 ml)and washed with water (5 x 100 ml). The organic layer was collected, dried over MgS04, filtered and evaporated. The residue was taken up in DCM and columned on silica gel using a gradient of 0 to 10% MeOH : DCM to afford compound 26 (65 mg, 0.143 mmol, 51 %).1H-NMR (CD3CN, 300 MHz): delta 1.58 (m, 2H), 1.75 (m, 2H), 2.22 (s, 1H), 2.40 (s, 3H), 2.42 (s, 1H), 2.44 (s, 3H), 3.01 (m, 4H), 3.39 (m, 3H), 6.20 (s, 1H), 6.37 (m, 1H), 7.25-7.60 (m, 4H), 8.36 (bs, 1H).

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; GILEAD SCIENCES, INC.; BABAOGLU, Kerim; BOOJAMRA, Constantine, G.; EISENBERG, Eugene, J.; HUI, Hon Chung; MACKMAN, Richard, L.; PARRISH, Jay, P.; SANGI, Michael; SAUNDERS, Oliver, L.; SIEGEL, Dustin; SPERANDIO, David; YANG, Hai; WO2011/163518; (2011); A1;,
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Electric Literature of 94838-59-2, A common heterocyclic compound, 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, molecular formula is C13H20N2O2, 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 mixture of l-methylpiperidine-4-carboxylic acid (500 mg, 3.49 mmol), HATU (1.59 g, 4T8mmol) and DIPEA (1.13 g, 8.73 mmol) in DCM (20 mL) was stirred at room temperature for 0.5 h. Then / -butyl 4-aminophenethylcarbamate (825 mg, 3.49 mmol) was added and the reaction was stirred at room temperature overnight. TLC showed the reaction completed. The reaction mixture was concentrated and purified by column chromatography to afford the title compound as white solid (170 mg, 13.5 % yield). ‘H NMR (500 MHz, DMSO-r/6) S: 9.75 (s, 1H), 7.49 (d, J= 8.4 Hz, 2H), 7.08 (d, J= 8.4 Hz, 2H), 6.82 (t, J= 5.3 Hz, 1H), 3.14 – 3.04 (m, 2H), 2.80 (d, J= 11.4 Hz, 2H), 2.62 (t, J= 7.5 Hz, 2H), 2.23 (ddd, J= 15.5, 7.8, 4.1 Hz, 1H), 2.15 (s, 3H), 1.91 – 1.79 (m, 2H), 1.66 (ddd, J= 17.6, 15.5, 6.7 Hz, 4H), 1.36 (s, 9H).

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; ZHEJIANG VIMGREEN PHARMACEUTICALS, LTD; SUN, Sanxing; ZHAO, Long; HU, Chongbo; CHEN, Zhengshu; YE, Jinqi; (0 pag.)WO2020/2969; (2020); A1;,
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Electric Literature of 53844-02-3, 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. 53844-02-3, name is Benzyl (2-bromoethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

According to the described general procedure (GP11), N-alkylation of commercially available 4(5)-methylimidazole (4.343 g ; 52.90 mmol) with (2-bromo-ethyl)-carbamic acid benzyl ester (15.019 g ; 58.19 mmol), and subsequent purification by FC (DCM /MeOH =10/1) afforded a mixture of [2-(4-methyl-imidazol-1-yl)-ethyl]-carbamic acid benzyl ester, and [2-(5-methyl-imidazol-1-yl)ethyl]-carbamic acid benzyl ester (ratio of regioisomers close to 1/1, according to 1H-NMR) as a yellow oil (4.270 g ; 31%). LC-MS: tR=0.68 min. (2 regioisomers); [M+H]+: 260.46 g/mol. A mixture of [2-(4-methyl-imidazol-1-yl)-ethyl]carbamic acid benzyl ester, [2-(5-methyl-imidazol-1-yl)-ethyl]-carbamic acid benzyl ester (1.198 g; 4.62 mmol; ratio of regioisomers close to 1/1, according to 1H-NMR), and 10% palladium on activated charcoal (240 mg; 20% in mass) was placed under nitrogen before addition of anh. MeOH (20 ml). The resulting mixture was placed under vacuum, and then under hydrogen (1 atm), and stirring at rt was continued for 2.5 h. Filtration over a pad of celite, concentration to dryness under reduced pressure afforded a mixture of 2-(4-methyl-imidazol-1-yl)-ethylamine, and 2-(5-methyl-imidazol-1-yl)-ethylamine as a slightly yellow oil (540 mg; 93%). LC-MS: tR=0.17 min. (2 regioisomers); [M+H]+: no ionisation. These primary amines were converted to the corresponding chlorhydrate salt by treatment of a solution of regioisomeric amines (540 mg ; 4.31 mmol) in dichloromethane (5 ml) with 4N HCl in 1,4-dioxane (3.25 ml ; 3 eq.). Concentration to dryness under reduced pressure afforded a beige solid which was further dried under HV.

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, Benzyl (2-bromoethyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Aissaoui, Hamed; Boss, Christoph; Koberstein, Ralf; Siegrist, Romain; Sifferlen, Thierry; US2011/105514; (2011); A1;,
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Some common heterocyclic compound, 5900-59-4, name is 2-Amino-4-chlorobenzamide, molecular formula is C7H7ClN2O, 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 2-Amino-4-chlorobenzamide

EXAMPLE 1 To a mixture of 7.73 g of 2-chloro-N-(3,4-dimetoxyphenethyl)acetamide, 5.12 g of 2-amino-4-chlorobenzamide, 13.5 g of sodium iodide and 3.63 g of magnesium oxide was added 30 ml of dimethylformamide and the resulting mixture was stirred at 90¡ã to 100¡ã C. for 4.5 hours. The reaction solution was concentrated under reduced pressure and the residue was extracted with 500 ml of chloroform. The chloroform extract was washed successively with 10percent hydrochloric acid, water, a 5percent aqueous sodium carbonate solution, a 5percent aqueous sodium sulfite solution and water, dried and then concentrated to dryness under reduced pressure. The residue was recrystallized from methanol to obtain 8.01 g of 2-(2-carbamoyl-5-chlorophenylamino)-N-(3,4-dimethoxyphenethyl)acetamide having a melting point of 167.5¡ã-168.5¡ã C. Elemental Analysis for C19 H22 O4 N3 Cl: Calcd. (percent): C, 58.24; H, 5.66; N, 10.72. Found (percent): C, 58.26; H, 5.59; N, 10.70.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5900-59-4, its application will become more common.

Reference:
Patent; Daiichi Seiyaku Co., Ltd.; US4297357; (1981); A;,
Amide – Wikipedia,
Amide – 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. 111300-06-2, name is tert-Butyl (trans-4-hydroxycyclohexyl)carbamate, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

Compound 2 (15 g, 57.47 mmol),trans-4-BOC-aminocyclohexanol (24.7g, 114.9mmol),Triphenylphosphine (30.1 g, 114.9 mmol) and 150 ml of THF were cooled to 0 C in an ice-salt bath.Add DIAD (23.2g, 114.9mmol) dropwise,Warm to room temperature and stir overnight.Column chromatography gave 13.1 g of solid, yield: 49.7%.

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; Shanghai Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Zheng Nan; Hao Qun; Zhou Weicheng; Lin Kuaile; Pan Jing; Chen Liang; Zhou Ting; Liu Zhenren; (39 pag.)CN110655519; (2020); A;,
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Synthetic Route of 79722-21-7, 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. 79722-21-7, name is tert-Butyl benzyloxycarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Nucleophile (1-3 mol equiv), tris-(dibenzylideneacetone)dipalladium (2.5 mol %), tris-(2-furyl)phosphine (10 mol %) and potassium carbonate (2 mol equiv) were added to a solution of the aryl halide (1 mmol) in dry dimethylformamide (10 mL) in a Schlenk tube. The reaction mixture was then degassed using the freeze, pump, thaw (F.P.T.) technique (one cycle). Allene gas was then introduced at the required pressure (1 atm) and the Schlenk tube contents stirred and heated at 80 C for 16 h. After cooling and venting, DCM (20 mL) was added and the mixture filtered to remove inorganic salts. The filtrate was concentrated in vacuo and the residue was purified by column chromatography.

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, tert-Butyl benzyloxycarbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Elboray, Elghareeb E.; Gao, Chuanjun; Grigg, Ronald; Tetrahedron; vol. 68; 14; (2012); p. 3103 – 3111;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 149423-70-1 as follows. HPLC of Formula: C14H20N2O2

Amine D1.1 (Prepared as described in Bauer, Shawn M.; Jia, Zhaozhong J.; Song, Yonghong; Xu, Qing; Mehrotra, Mukund; Rose, Jack W.; Huang, Wolin; Venkataramani, Chandrasekar; Pandey, Anjali. PCT mt. Appi. (2009), W02009145856A1.) (1.92 g, 7.7 mmol) was diluted with dichioromethane (30 mL) affording an opaque solution. To this was added di-tbutyl dicarbonate (2.0 g, 9.3 mmol) in two portions. The resulting solution was then stirred for approximately 1 hr at which time the reaction was determined to be complete by UPLC. The reaction mixture was then concentrated and dried in vacuo overnight affording 2.47 g of the diprotected diamine as a light pink syrup. MS found for C11H21N202 as (M – Boc+2H) 249.2 and (M+Na)+ = 371.4.

According to the analysis of related databases, 149423-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; JIA, Zhaozhong J.; KANE, Brian; XU, Qing; BAUER, Shawn M.; SONG, Yonghong; PANDEY, Anjali; DICK, Ryan; WO2013/78468; (2013); A1;,
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Application of 3144-09-0, These common heterocyclic compound, 3144-09-0, name is Methylsulfonamide, 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.

CH2Cl2 (3.06 ml) was added to the 20 mL Scint vial containing DMAP (5.61 mg, 0.046 mmol), 2-chloro-1-methylpyridin-1-ium iodide (0.282 g, 1.102 mmol), benzoic acid 1a (0.1122 g, 0.919 mmol), methanesulfonamide 2a (0.175 g, 1.837 mmol) at room temperature. After stirring for 5 min, TEA (0.38 ml, 2.76 mmol) was slowly added to the reaction mixture. The reaction was stirred at room temperature for 1 hour. The reaction solvent was removed via vacuum and the crude was taken up in ethyl acetate, washed with 1N HCl. The ethyl acetate layer was separated, dried (Na2SO4), filtered and concentrated. The crude was purified by flash column eluted with ethyl acetate in hexane from 0 to 50% to 100% to give the desired product 3a as a white solid. (0.1409 g, 77%). 1H NMR (400 MHz, CHLOROFORM-d) delta 8.96 (br s, 1H), 7.95 – 7.82 (m, 2H), 7.68 – 7.61 (m, 1H), 7.56 – 7.49 (m, 2H), 3.46 (s, 3H); 13C NMR (126 MHz, CHLOROFORM-d) delta 165.5, 133.9, 131.0, 129.1, 127.9, 41.8; HRMS(ESI-) : observed: 198.0221; theory: 198.0217.

The synthetic route of 3144-09-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Ling; Luo, Guanglin; Tetrahedron Letters; vol. 60; 3; (2019); p. 268 – 271;,
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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. 147356-78-3, name is N-Methoxy-N-methylcyclopropanecarboxamide, A new synthetic method of this compound is introduced below., Product Details of 147356-78-3

To a mixture of (5S,7S)-2-bromo-5-(2,5-difluorophenyl)-7-fluoro-6,7-dihydro-5H-pyrrolo[l,2- b][l,2,4]triazole (100 mg, 0.31 mmol), N-methoxy-N-methyl-cyclopropanecarboxamide (81 mg, 0.63 mmol) in tetrahydrofuran (3 mL) was added isopropylmagnesium chloride (2.0 M in tetrahydrofuran, 0.31 mL, 0.63 mmol) dropwise at 0 C. The mixture was stirred at 0 C for 0.5 h and quenched by addition of saturated aqueous ammonium chloride (10 mL). The mixture was extracted with ethyl acetate (3 x 10 mL). The combined organic layers were washed with water (20 mL), brine (20 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC to give cyclopropyl-[(5S,7S)-5-(2,5-difluorophenyl)-7-fluoro-6,7-dihydro-5H- pyrrolo[l ,2-b][l,2,4]triazol-2-yl]methanone (22.1 mg, 23%) as a white solid. H NMR (400 MHz, CD3OD) delta 7.28 – 7.17 (m, 2H), 6.93 – 6.88 (m, 1H), 6.22 – 6.06 (m, 1H), 5.90 – 5.86 (m, 1H), 3.88 – 3.74 (m, 1H), 3.09 – 3.02 (m, 1H), 2.93 – 2.82 (m, 1H), 1.21 – 1.18 (m, 2H), 1.15 – 1.11 (m, 2H). LCMS RT = 1.007 min, m/z = 308.1 [M+H]+. LCMS (10 to 80%o acetonitrile in water + 0.03%o trifluoacetic acid over 2 mins) retention time 1.007 min, ESI+ found [M+H] = 308.1.

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; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); A1;,
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