Tag: M.W=100-200

Related Products of 112257-19-9, These common heterocyclic compound, 112257-19-9, name is tert-Butyl methyl(2-(methylamino)ethyl)carbamate, 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.

Preparation Example 1-3: Preparation of Compound (II-4)[0060][0061] Under an argon stream, 4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl (4-nitrophenyl) carbonate (6.8 g, 9.22 mmol) was dissolved in 150 mL of anhydrousdimethylformamide, and stirred, together with t-butyl methyl(2-(methylamino)ethyl)carbamate (1.82 g, 9.68 mmol) at 20- 25¡ãC for 19 hrs. After completion of the reaction, the reaction mixture was completely concentrated in a high vacuum,and the concentrate was purified by silica gel column chromatography to obtain an amino-protected derivative of compound (II-4) (5.14 g, 71percent).[0062]1H NMR (400 MHz, DMSO-d6) delta0.78-0.8 (d, 3 H), 0.8-0.83 (d, 3 H), 1.09 -1.99 (m, 10 H), 1.33 (s, 9 H), 1.92(m, 1 H), 2.07-2.19 (m, 2H), 2.66-2.73 (d, 3H), 2.8-2.81 (m, 3H), 2.9-3.0 (m, 2H), 3.37 (m, 2 H), 4.15 (t, 1 H), 4.34 (m,1 H), 4.94 (s, 2 H), 5.38 (s, 2 H), 5.94 (brt, 1 H), 6.96 (s, 2H), 7.23 (d, 2 H), 7.55 (d, 2 H), 7.77 (d, 1 H), 8.04 (d, 1 H),9.95 (brs, 1 H)[0063] LC-MS m/z: 787.5 [M+H]+[0064] With the exception of using the amino-protected derivative of compound (II-4), the same procedure as inPreparation Example 1-2 was repeated to obtain a concentrated TFA salt of the title compound.

The synthetic route of 112257-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Celltrion, Inc.; PARK, Young Jun; JEONG, Jin-kyo; CHOI, Young Mi; LEE, Minseob; KIM, Yeon Jung; KIM, Kyoung Suk; CHOI, Joon hun; LEE, Jin Seo; CHO, Eun Joo; SONG, Hyunnam; PARK, Sung Jun; LEE, Jong-hyoup; LEE, Matthew Sangyup; LEE, In-Suk; KIM, Joon woo; HONG, Seung Suh; EP2927227; (2015); 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. 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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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;,
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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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Electric Literature of 226260-01-1, 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. 226260-01-1, name is 3-Fluoro-N-methoxy-N-methylbenzamide, This compound has unique chemical properties. The synthetic route is as follows.

Example 5 1-(3-FLUOROPHENYL) BUTAN-1-ONE To a solution of 3-fluoro-N-methoxy-N-methylbenzamide (130 mg, 0.71 mmol) in dry THF (2 mL) cooled to-10 C was added propyl magnesium chloride (532 ul, 2M solution in ether, 1.1 mmol) under nitrogen. The solution was stirred at-10 C for Ih and at room temperature for 75 min. The solution was the poured into saturated aqueous ammonium chloride and the product extracted into ethyl acetate (3 x 25 mL). The organic layers were combined, washed with brine, dried (MGSO4) and concentrated to give a pale yellow oil, which was purified by chromatography using ethyl acetate-hexane (1: 9) to separate the pure product (78 mg, 66%). ‘H-N. m. r. (CDCl3) No. 1.01 (t, =7. 4Hz, 3H, Me), 1.77 (sep, 2H, CH2CH3), 2.93 (T, J=7. 2Hz, 2H, COCH2), 7.15-7. 30 (m, 1H, Ar), 7.35-7. 50 (m, 1H, Ar), 7.60-7. 70 (m, 1H, Ar), 7.70-7. 80 (m, 1H, Ar.

The chemical industry reduces the impact on the environment during synthesis 3-Fluoro-N-methoxy-N-methylbenzamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CYTOPIA PTY LTD; WO2004/52868; (2004); A1;,
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55512-05-5, name is 3-(Methylsulfonamido)benzaldehyde, belongs to amides-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: 55512-05-5

N-(3-formylphenyl)methanesulfonamide (465 mg, 2.33 mmol) was dissolved in acetone (10 mL) at room temperature. Powdered K2C03 (968 mg, 7.00 mmol) and iodomethane (0.29 mL, 4.67 mmol) were then added and the reaction mixture allowed to stir overnight. The reaction mixture was poured into water (5 mL) and extracted with EtOAc (3 x 15 mL). The combined organic phases were washed with brine (5 mL),dried over MgSO4 and concentrated to give crude product which was carried on without further purification.

The synthetic route of 55512-05-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; BACON, Elizabeth, M.; BALAN, Gayatri; CHOU, Chien-hung; CLARK, Christopher, T.; COTTELL, Jeromy, J.; KIM, Musong; KIRSCHBERG, Thorsten, A.; LINK, John, O.; PHILLIPS, Gary; SCHROEDER, Scott, D.; SQUIRES, Neil, H.; STEVENS, Kirk, L.; TAYLOR, James, G.; WATKINS, William, J.; WRIGHT, Nathan, E.; ZIPFEL, Sheila, M.; (640 pag.)WO2017/7694; (2017); A1;,
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Electric Literature of 6973-09-7, 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. 6973-09-7 name is 5-Amino-2-methylbenzenesulfonamide, 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.

Example 60: Process for the preparation of PZP.HCI[000177] A 250 mL reactor equipped with a mechanical stirrer was charged with CPM I (4.84 g, 16.82 mmol), AMBS (3.29 g, 17.66 mmol, 1 .05 eq) and 90% acetic acid (29 mL, 6V) and the reaction mixture was heated to 55 C with stirring, leading to dissolution. After 3.5 h precipitation commenced and the reaction was continue for 22 h in total. The resulting mixture was then heated to 65 C over 0.5 h and stirring was continued at the same temperature for an additional 5 h. The reaction mixture was then heated to 100 C over 1 h leading to complete dissolution. Stirring was continued at the same temperature for 0.5 h and then EtOH abs. (48 mL, 10V) was added drop-wise with concomitant cooling to 80 C over a period of 0.5 h. The mixture was then cooled to 0 C over a period of 4 h and stirring was continued at the same temperature for 16 h. The solids were filtered and the filter cake was washed with EtOH abs. (4x 14.5 mL, 4×3 V) at Patent ApplicationAtty Docket No. 14669.0172 WOU 1 room temperature and dried in a vacuum oven (35 mbar) at 60 C for 22 h to give pure PZP.HC1 (7.05 g, 88.5% yield, 99.4% assay, 99.9% purity, 7.32% CI, CPMI < 20 ppm) as a beige powder. At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Amino-2-methylbenzenesulfonamide, and friends who are interested can also refer to it. Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; RENDELL, Jacob; KWOKAL, Ana; WO2011/69053; (2011); A1;,
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Application of 113778-69-1, 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. 113778-69-1, name is N-Methoxy-N-methylisobutyramide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

n-Butyllithium (2.5 M in n-hexane, 22.0 mL, 44.4 mmol) was added dropwise to a – 80 C solution of 2-bromo-5-(trifluoromethyl)pyridine (5.0 g, 22.1 mmol) in THF (35 mL), and the resulting solution stirred for 10 minutes. N-methoxy-N-methylisobutyramide (3.49 g, 26.61 mmol) was added at -80 C, and the reaction mixture stirred for 1 h at -80 C. The reaction was then quenched by the addition of 40 mL of saturated aqueous ammonium chloride solution, and the mixture was allowed to warm to room temperature. The resulting solution was extracted with 3×40 mL of ethyl acetate, and the combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 1 :7 ethyl acetate/petroleum ether) to give 2-methyl-l-(5-(trifluoromethyl)pyridin-2-yl)propan-l-one (550 mg, 8% yield) as a yellow solid. MS (ESI, m/z): 218 [M+H]+.

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, N-Methoxy-N-methylisobutyramide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; MARTIN, Matthew W.; NG, Pui Yee; THOMASON, Jennifer R.; HAN, Bingsong; RUDNITSKAYA, Aleksandra; LANCIA, JR., David R.; (180 pag.)WO2019/204550; (2019); A1;,
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Reference of 1129-26-6, A common heterocyclic compound, 1129-26-6, name is 4-Methoxybenzenesulfonamide, molecular formula is C7H9NO3S, 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) 0.0040g iridium catalyst [Cp * IrCl2] 2,0.0076 g silver salt bis(trifluoromethanesulfonyl)imide silver,0.825g oxidant silver acetate,31.4 muL acetophenone-O-methyl oxime and0.0748 g of p-methoxybenzenesulfonamide was placed in a reaction tube.Add 2mL of dichloromethane as a solvent,Heating and stirring reaction,The temperature of heating and stirring is 60C.Reaction time 24h.(2) After the reaction is over,Separation by column chromatography (300-400 column chromatography silica gel column packing,Eluent: ethyl acetate: petroleum ether = 12:100 v/v),Can get the productN-[2-(1-Methoxyimino)ethyl]phenyl-4-methoxybenzenesulfonamide.Yield 97%

The synthetic route of 1129-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; University of Jinan; Zhao Huaiqing; Zhang Wei; Xu Xiangwen; Wu Wei; (40 pag.)CN107739322; (2018); A;,
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These common heterocyclic compound, 50667-69-1, name is 2,2,2-Trifluoro-N-(hydroxymethyl)acetamide, 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. Computed Properties of C3H4F3NO2

To a solution of 2-chloro-6-methylbenzoic acid (2.0 g, 11.72 mmol) in cone H2SO4 (4 mL) was added 2,2,2-trifluoro-N-(hydroxymethyl)acetamide (1.26 g, 8.80 mmol). The mixture was stirred at rt for 16 h. The reaction mixture was poured into ice-water and stirred for 2 h. The precipitate was collected by filtration and dried to afford 1.80 g of the title product and 6- chloro-2-methyl-3-((2,2,2-trifluoroacetamido)methyl)benzoic acid as mixture of products. A solution of 2-chloro-6-methyl-3-((2,2,2-trifluoroacetamido)methyl)benzoic acid (1.70 g, 5.75 mmol) in cone. HC1 (10 mL) and dioxane (2 mL) was heated at reflux for 12 h. The reaction mixture was concentrated and the concentrate was dissolved in THF (1 mL). The solution was treated with NaOH (690 mg, 17.25 mmol) in H20 (2 mL) at 0C followed by iert-butyl dicarbonate (2.51 g, 11.50 mmol). The reaction mixture was stirred rt for 16 h. The reaction mixture was acidified with IN HC1 and the pH was adjusted to 2-3. The reaction mixture was extracted with 5% MeOH in CHCl3. The organic layer was separated, dried, filtered and concentrated. The concentrate was dissolved in CH3CN (20 mL) and the solution was treated with K2CO3 (1.60 g, 11.50 mmol) and CH3I (11.50 mmol) at rt. Then the reaction mixture was heated at 50 C for 1-2 h before it was quenched with water and was extracted with EtOAc. The organic layer was washed with brine, separated, dried, filtered and concentrated. The concentrated was purified by column chromatography to provide 1.4 g of the title product and methyl 3-(((ierf-butoxycarbonyl)amino)methyl)-6-chloro-2- methylbenzoate as mixture of products.

The synthetic route of 2,2,2-Trifluoro-N-(hydroxymethyl)acetamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; BANERJEE, Abhisek; PAWAR, Mahesh Yashwant; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2013/38308; (2013); A1;,
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