Amides-buliding-blocks

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. 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows., 67442-07-3

(d) To a solution of 0.33 g (0.83 mmol) 3-acetoxy-4-fluoro-N-[4-(imidazol-1-yl)-3-trifluoromethylphenyl]-benzamide, J-1c, in 5 mL acetone and 0.5 mL of methanol was added cesium carbonate (0.54 g, 1.65 mmol) and 2-chloro-N-methoxy-N-methyl-acetamide (0.15 g, 1.07 mmol) and the resulting mixture was stirred for 6 h at 45¡ã C. After cooling to room temperature, the mixture was partitioned between ethyl acetate and sat. brine (2*20 mL). The organic layer was filtered though a silica gel plug and concentrated. The residue was purified by titurated with diethyl ether (2*20 mL) to give 0.35 g (92percent) of 4-fluoro-N-[4-(imidazol-1-yl)-3-trifluoromethylphenyl]-3-[(N-methoxy-N-methylcarbamoyl)methoxy]benzamide, J-1d, as a white solid: Rt=11.95 min.; 1H NMR (300 MHz, CDCl3) delta8.34 (d, 1H, J=2.4 Hz), 8.11 (dd, lh, J=8.7 Hz), 7.64-7.54 (m, 3H), 7.42 (d, 1H, J=8.7 Hz), 7.22-7.15 (m, 2H), 6.97 (s, 1H), 502 (s, 2H), 3.72 (s, 3H), 3.06 (s, 3H); MS (ESI): Calculated for C21H18F4N4O4 (M+H+): 467, Found: 467.

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Reference:
Patent; Bender, Steven Lee; Bhumralkar, Dilip; Collins, Michael Raymond; Cripps, Stephen James; Deal, Judith Gail; Jia, Lei; Nambu, Mitchell David; Palmer, Cynthia Louise; Peng, Zhengwei; Varney, Michael David; US2002/103203; (2002); A1;,
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354-38-1, These common heterocyclic compound, 354-38-1, name is 2,2,2-Trifluoroacetamide, 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 Trifluoroacetamide (1.2 g, 10.6 mmol), Lawesson’s reagent (2.36 g, 5.84 mmol) and THF (10 mL) was heated at reflux for 2 h.The mixture was concentrated and purified by chromatography to give the sub-title compound (0.89 g, 6.9 mmol, 65 %).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 354-38-1.

Reference:
Patent; ATROGI AB; PELCMAN, Benjamin; BENGTSSON, Tore; (93 pag.)WO2019/53427; (2019); A1;,
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6331-71-1, A common heterocyclic compound, 6331-71-1, name is 4-Amino-N,N-dimethylbenzamide, molecular formula is C9H12N2O, 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.

Step 3: Synthesis of methyl 5-(N-(4- (dimethylcarbamoyl)phenyl)sulfamoyl)thiophene-2-carboxylate (Intermediate 75) To a solution of 4-amino-N,N-dimethylbenzamide (Int. 74) (57 g, 347 mmol) in pyridine (570 L, 7.06 mmol) kept at 0 degrees in an ice/water bath, methyl 5-(chlorosulfonyl)thiophene-2-carboxylate (100 g, 417 mmol) was added and the mixture stirred at 0 degrees for 3hr. The reaction mixture was diluted with HCl IN and extracted with AcOEt (x2). The organic phase was dried over Na2SO4 and concentrated under vacuum to give 100 mg of 5-(N-(4- (dimethy lc arb amoy l)pheny 1) sulf amoy l)thiophene -2 -carb oxy late (Int . 75).

The synthetic route of 6331-71-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIESI FARMACEUTICI S.p.A.; ARMANI, Elisabetta; CAPALDI, Carmelida; CARZANIGA, Laura; ESPOSITO, Oriana; WO2013/182451; (2013); A1;,
Amide – Wikipedia,
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Adding some certain compound to certain chemical reactions, such as: 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, 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 67442-07-3. 67442-07-3

into the reactor add LD-I and tetrahydrofuran; Replace nitrogen 3 times, under nitrogen protection, cool the solution at-12 C, slowly add 2N iso-propylmagnesium chloride THF solution, the resulting reaction solution is stirred at -12C for 1h, until the reaction is complete, dissolve 2-chloro-N-methoxyl-N-methylacetamide into methyl tert-butyl ether, after that slowly add 2-chloro-N-methoxyl-N-methylacetamide solution into the reactor, while dropping, keep the internal temperature at -10C, adjust the internal temperature at 0C and continue stirring for 2 hours, after the reaction is completed, 1N hydrochloric acid is added and the layers are separated, and extracting the aqueous layer with methyl tert-butyl ether, combining organic layers, concentrate under reduced pressure at 10 volumes, adjust the temperature at 20 C, and stir for 1.5h, centrifuge, and wash the filter cake with isopropyl alcohol, dried, and obtained solid product LD-J.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2-Chloro-N-methoxy-N-methylacetamide.

Reference:
Patent; Anhui Nuoquan Pharmaceutical Co., Ltd.; Du Xiaopeng; Xu Liangzhi; Hu Zhigang; He Darong; Qian Zhujin; He Yong; Liu Zhuangzi; (12 pag.)CN107879908; (2018); A;,
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631-58-3, 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. 631-58-3, name is Propanethioamide, This compound has unique chemical properties. The synthetic route is as follows.

Example 11 2-ethyl-5-(2-fluoro-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazole A solution of 2-bromo-2-(2-fluoro-4-pyridyl)-1-(3-methylphenyl)ethanone hydrobromide (11 g, 29 mmol) and thiopropionamide (2.7 g, 30 mmol) in N,N-dimethylformamide (30 mL) was stirred for 14 hours at room temperature. Aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and extracted with ethyl acetate. The extracts were washed with water, dried, then, the solvent was distilled off. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1) to obtain a title compound (3.3 g, yield 38%). Oil 1H-NMR (CDCl3) delta: 1.64 (3H, t, J=7.6 Hz), 2.34 (3H, s), 3.10 (2H, q, J=7.6 Hz), 6.84-6.86 (1H, m), 7.05-7.09 (1H, m), 7.13-7.25 (3H, m), 7.37 (1H, s), 8.10 (1H, d, J=5.6 Hz).

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; Ohkawa, Shigenori; Naruo, Ken-ichi; Miwatashi, Seiji; Kimura, Hiroyuki; US2004/53973; (2004); A1;,
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Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 283173-80-8, name is 2-Bromo-8-fluoro-4,5-dihydro-1H-azepino[5,4,3-cd]indol-6(3H)-one, belongs to amides-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 283173-80-8, 283173-80-8

l, r-Bis(diphenylphosphino)ferrocene palladium (II) dichloride (2.5 moles, 1.83 kg) was added to a solution of Formula-Al (1.0 moles) in a 1:2 mixture of 4.2 L of dichloromethane and degassed dimethylacetamide. The reaction mass was stirred for 1 hour at about 20 C. Thereafter, the reaction mixture temperature was raised to 95 C and stirred for 1 hour. In a separate vessel, Formula-C3 (1.2 moles) was dissolved in dimethylacetamide (1.1 L) and added to 2.8 L of an aqueous solution of sodium carbonate (2.0 moles) and stirred for 3 hours at 20 C. The contents of the separate vessel were added to the first reaction mixture, maintaining the temperature above 90 C. The combined reaction mixture was stirred for 2 hours, cooled to room temperature, and further stirred for 4 hours. Water (2.8 L) was added to the reaction mixture which was filtered. The obtained solid was crystallized in methanol to obtain a compound of Formula-B 1.

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, 2-Bromo-8-fluoro-4,5-dihydro-1H-azepino[5,4,3-cd]indol-6(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MYLAN LABORATORIES LTD; JAYACHANDRA, Sureshbabu; SETHI, Madhuresh; KAUSHIK, Vipin Kumar; RAVI, Vijaya, Krishna; TELAGAMSETTY, Bhaskar Kumar; (44 pag.)WO2019/130229; (2019); A1;,
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127828-22-2,Some common heterocyclic compound, 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, molecular formula is C9H20N2O3, 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.

tert-Butyl 2-(2-aminoethoxy)ethylcarbamate (570 mg, 2.8 mmol) was taken up in CH3CN (8 mL) and DMF (8 mL) along with Acipimox (435 mg, 2.8 mmol) HATU (1.17 g, 3.1 mmol) and DIEA (730 muL, 4.2 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It was then diluted with EtOAc (50 mL), washed with water (3*10 mL), brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (9:1 CH2Cl2/MeOH) to afford 5-((2-(2-((tert-butoxycarbonyl)amino)ethoxy) ethyl)carbamoyl)-2-methylpyrazine 1-oxide (810 mg, 85%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, its application will become more common.

Reference:
Patent; Milne, Jill C.; Jirousek, Michael R.; Bemis, Jean E.; Vu, Chi B.; US2011/82156; (2011); A1;,
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3144-09-0, 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. 3144-09-0, name is Methylsulfonamide, This compound has unique chemical properties. The synthetic route is as follows.

In a 2-liter reaction flask, 1 liter of ethyl acetate and 66 grams of methylsulfonamide were added, and 109 grams of chloroacetyl chloride was gradually added; the temperature was gradually increased to 65C for 12 hours until the end of the reaction.The reaction solution gradually cooled to 0 degree, and a large amount of white solid precipitated; it was filtered and dried to obtain 112 g of solid SLP-10b (X=Cl).Yield: 94%.H NMR (400MHz, CDCl3): delta 4.02 (s, 2H), 3.28s, 3H)ESI/MS+(m/z):171

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Reference:
Patent; Shanghai Aikangrui Pharmaceutical Technology Co., Ltd.; Fan Linfeng; Zhu Yangwei; Qiu Aiyun; Lv Bojie; Xu Zhonghui; Zhang Changxuan; (11 pag.)CN106316967; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

2886-65-9, 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. 2886-65-9, name is 7-Chloro-5-(2-fluorophenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 1 7-Chloro-5-(2-fluorophenyl)-2-methylamino-3H-1,4-benzodiazepine A solution of 200 g. (0.695 m) of 7-chloro-1,3-dihydro-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one in 2 l. of tetrahydrofuran and 250 ml. of benzene was saturated with methylamine with cooling in an ice bath. A solution of 190 g. (1 m) of titaniumtetrachloride in 250 ml. of benzene was added through a dropping funnel within 15 minutes. After addition the mixture was stirred and refluxed for 3 hours. Water, 600 ml., was added slowly to the cooled reaction mixture. The inorganic material was separated by filtration and was washed well with tetrahydrofuran. The water layer was separated and the organic phase was dried over sodiumsulfate and evaporated. The crystalline residue was collected with m.p. 204-206. The analytical sample was recrystallized from methylene chloride/ethanol, m.p. 204-206.

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; Hoffmann-La Roche Inc.; US4280957; (1981); A;,
Amide – Wikipedia,
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177906-48-8, The chemical industry reduces the impact on the environment during synthesis 177906-48-8, name is trans-N-Boc-1,4-cyclohexanediamine, I believe this compound will play a more active role in future production and life.

[0311] To a stirred solution of 5-cyclopropyl-4-iodoisoxazole-3-carboxylic acid (1.0 g, 3.59 mmol) in DMF (10 ml) was added EDCI (0.892 g, 4.66 mmol) and HOBT (0.533 g, 3.94 mmol). The solution was stirred for 10 min at 0 C. Next tert-butyl ((lr,4r)-4- aminocyclohexyl)carbamate (0.769 g, 3.59 mmol) was added and the reaction was stirred at rt for 2hr. The progress of the reaction was monitored by TLC. After complete consumption of starting material, the reaction was quenched with water and the solid precipitated was collected by filtration and dried under reduced pressure to obtain a residue. The material was purified by column chromatography to afford tert-butyl ((lr,4r)-4-(5-cyclopropyl-4-iodoisoxazole-3-carboxamido)cyclohexyl)carbamate (0.48 g, 28 %).

The chemical industry reduces the impact on the environment during synthesis trans-N-Boc-1,4-cyclohexanediamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; EPIZYME, INC.; FOLEY, Megan Alene Cloonan; KUNTZ, Kevin Wayne; MILLS, James Edward John; MITCHELL, Lorna Helen; MUNCHHOF, Michael John; HARVEY, Darren Martin; (208 pag.)WO2016/40498; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics