Category: amides-buliding-blocks

7341-96-0, The chemical industry reduces the impact on the environment during synthesis 7341-96-0, name is Propiolamide, I believe this compound will play a more active role in future production and life.

N-Chlorosuccinimide (624 mg, 4.7 mmol) was added in portions to a solution of 4- bromomethyl-benzaldehyde oxime (which may be prepared as described in Charrier, J.-D. et al. WO2011/143426 p 77; 1 g, 4.7 mmol) in DMF (9 mL) at room temperature. The reaction mixture was stirred for 2 h under argon. The mixture was poured into ice-water and this was extracted with Et2O (3 x 50 mL). The combined organic layers were washed with brine, dried (Na2SO4) and evaporated to give a solid (1.4 g). The solid was dissolved in 50% aqueous tert-butanol (20 mL) in a flask that was open to the air. Propiolamide (which may be prepared as described in Matsumoto, T. et al. US 7,851,473 Column 128; 323 mg, 4.7 mmol) was added, followed by 1 M sodium ascorbate (0.47 mL, 0.47 mmol) and 0.1 M copper(II) sulfate (2.34 mL, 0.23 mmol). KHCO3 (1.87 g, 18.7 mmol) was added in portions and the reaction mixture was stirred at room temperature for 3 h. H2O (25 mL) was added and the mixture was extracted with 85: 15 CHCl3/CH3OH (3 x 100 mL). The combined organic layers were washed with brine, dried (Na2S04), filtered, evaporated, and purified by chromatography (16-20% acetone/CH2Cl2) to give 3-(4-bromomethyl- phenyl)-isoxazole-5-carboxylic acid amide (156 mg, 12%). Purification of mixed fractions by chromatography (16-20% acetone/CH2Cl2) provided a further 40 mg (3%) of 3-(4- bromomethyl-phenyl)-isoxazole-5-carboxylic acid amide.

The chemical industry reduces the impact on the environment during synthesis Propiolamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ERICKSON, Shawn, David; GILLESPIE, Paul; MERTZ, Eric; WO2014/86704; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

112101-81-2, A common compound: 112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, belongs to amides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

7.0 g of recrystallised (-)-(R)-5-(2-(2-(2-ethoxyphenoxy) ethylamino)-1-propyl)-2- methoxybenzenesulphonamide hydrochloride (TH) from Example 3 is recrystallised from mixtures of methanol and ethanol. Analysis : Methanol to HPLC-composition of Quantity Yield HPLC-composition of ethanol the starting raw of solvent the product* ratio material* used 100 : 0 TH 95. 84 % 90 ml 5. 44 g TH 97. 77 % impurity (2) 0. 09 % (77. 7%) impurity (2) 0. 0 % impurity (3) 0. 0 % impurity (3) 0. 0 % impurity (4) 0. 24 % impurity (4) 0. 04 % impurity (5) 0. 05 % impurity (5) 0. 0 % impurity (6) 3. 73 % impurity (_) 2. 19 % 90 : 10 TH 95. 5 % 110 ml 5. 64 g TH 97. 53 % impurity (2) 0. 12 % (80. 6%) impurity (2) 0. 12 % impurity (3) 0. 0 % impurity (3) 0. 0 % impurity (4) 0. 31 % impurity (4) 0. 06 % impurity (2 0. 08 % impurity (5) 0. 00 % impurity (6) 3. 94 % impurity (6) 2. 41 % 70 : 30 TH 95. 9 % 160 ml 5. 70 g TH 99. 89 % impurity (2) 0. 12 % (81. 4%) impurity (2) 0. 0 % impurity (3) 0. 0 % impurity (3) 0. 0 % impurity 0. 31 % impurity (4) 0. 05 % impurity (5) 0. 08 % impurity (5) 0. 0 % impurity (6) 3. 49 % impurity (6) 0. 0 % 50 : 50 TH 99. 27 % 230 ml 5. 95g TH 99. 85 % impurity (2) 0. 15 % (85. 0%) impurity (2) 0. 0 % impurity (3) 0. 0 % impurity (3) 0. 0 % impurity (4) 0. 32 % impurity (4) 0. 06 % impurity (5) 0. 08 % impurity (5) 0. 0 % impurity (6) 0. 0% impurity 0. 0% 30 : 70 TH 99. 28 % 340ml 5. 98 g TH 99. 81 % impurity (2) 0. 17 % (85. 4%) impurity (2) 0. 02 % impurity (3) 0. 0 % impurity (3) 0. 0 % impurity (4) 0. 32 % impurity (4) 0. 08 % impurity (5) 0. 10 % impurity (5) 0. 0 % impurity (6) 0. 0 % impurity (6) 0. 0 % * impurity (2) = 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide impurity (3) = 2-(2-ethoxyphenoxy) ethylbromide impurity N- (2- (2-ethoxyphenoxy) ethyl)-5- (2- (2- (2-ethoxyphenoxy) ethyl) amino)-1-propyl)-2-methoxybenzenesulphonamide impurity (5) = 5-(2-(bis-(2-(2-ethoxyphenoxy) ethyl) amino)-1-propyl)-2-methoxybenzenesulphonamide impurity (6) = 1,2-bis (2-ethoxyphenoxy) ethane (6)

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, R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; WO2005/63702; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common compound: 16982-21-1, name is Ethyl 2-amino-2-thioxoacetate, belongs to amides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 16982-21-1

N,6-dimethylnicotinohydrazide (23a, 0.1 g, 0.61 mmol) and ethyl 2-amino-2-thioxoacetate (0.089 g, 0.67 mmol) in toluene (0.5 mL) and acetic acid (0.05 mL) were stirred at 90 C for 10 hours. The reaction mixture was purified by preparative HPLC using a Gemini NX reverse-phase column (C-18, 5 microns silica, 30 mm diameter, 150 mm length, flow rate of 60 ml / minute) using an isocratic mixture of 17% acetonitrile in water (containing ammonium carbonate (2 g / L). The fractions containing the desired compound were evaporated to dryness to afford ethyl 1-methyl-5-(6-methylpyridin-3-yl)-1H-1,2,4-triazole-3-carboxylate (34a, 0.083 g, 55%) as a yellow crystalline solid: 1H NMR (500 MHz, DMSO-d6) delta 8.87 (d, J = 1.9 Hz, 1H), 8.13 (dd, J = 1.9, 8.1 Hz, 1H), 7.49 (d, J = 8.1 Hz, 1H), 4.36 (q, J = 7.1 Hz, 2H), 4.06 (s, 3H), 2.58 (s, 3H), 1.33 (t, J = 7.1 Hz, 3H); 13C NMR (126 MHz, DMSO-d6) delta (ppm) 161.34, 158.91, 156.03, 151.34, 150.14, 136.39, 124.11, 118.93, 63.45, 37.12, 24.34, 14.38; HRMS, ESI+ m/z, (M+H)+ calculated for C12H14N4O2 257.10330; found, 247.11879 (tR = 1.20 min., purity = 100%).

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, 16982-21-1, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Degorce, Sebastien; Delouvrie, Benedicte; Davey, Paul R.J.; Didelot, Myriam; Germain, Herve; Harris, Craig S.; Brempt, Christine Lambert-Van Der; Lebraud, Honorine; Ouvry, Gilles; Tetrahedron Letters; vol. 53; 45; (2012); p. 6078 – 6082;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

78888-18-3, 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. 78888-18-3, name is tert-Butyl allylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of N-tert-butoxycarbonyl prop-2-enylamine 2A(20 g, 127.39 mmoL) was dissolved in Nu, Nu-dimethylformamide (100 mL), sodium sulphate(7.6 g, 60 / , 191.08 mmoL) was treated with n-hexane and then added with N, N-dimethylformamide (400 mL) and added dropwise to the reaction solution at 0 C under nitrogen C for 30 minutes, and the reaction was continued at room temperature for 20 minutes.A mixture of proparagyl bromide (30.3 g, 245.78 mmoL) was added dropwise to the ice bath and the mixture was stirred at 0 C for 30 minutes. The reaction solution was slowly added to crushed ice to deal with excess sodium hydride, extracted with ethyl acetate (100 mL chi3), the organic phases were combined and washed with saturated brine (100 mL x 3), dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure The The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (nu / nu) = 100: 1 to 50: 1) to give yellow liquid 2B (21 g, yield 85%).

The synthetic route of 78888-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SICHUAN HAISCO PHARMACEUTICAL CO., LTD; FAN, JIANG; FENG, JIAN-CHUAN; PENG, FEI; CHEN, QING-PING; (89 pag.)TW2017/8224; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

57561-39-4, These common heterocyclic compound, 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)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.

2-(Boc-methyl-amino)-ethanol (0.19 g, 1 mmol) was dissolved in 4 mL of dichloromethane, and added with Dess-Martin periodinane (0.64 g, 1.5 mmol), and stirred at room temperature for 1 hour. 3 mL of a saturated sodium thiosulfate solution and 5 mL of a saturated sodium bicarbonate solution were added to the reaction mixture, and the mixture was stirred until clarified. Then, it was extracted with 20 mL of dichloromethane, and the dichloromethane layer was concentrated under reduced pressure. The residues were dissolved in 5 mL of acetic acid, and added with ethyl 5-bromo-3-amino-2-methyl-benzoate 1c (0.26 g, 1 mmol). The sodium borohydride (0.22 g, 6 mmol) was added portionwise and then stirred at room temperature for 0.5 hour. The reaction solution was added with water and ethyl acetate. The ethyl acetate layer was washed with aqueous solution of sodium hydroxide. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residues were purified by column chromatography (eluent: petroleum ether:ethyl acetate 30:1 to 3:1) to give 0.3 g of title product.

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 57561-39-4.

Reference:
Patent; ANCUREALL PHARMACEUTICAL (SHANGHAI) CO., LTD.; Si, Jutong; Wang, Guan; Jiang, Meifeng; YANG, Zhihe; Zhou, Chentao; (118 pag.)US2019/345139; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 22227-26-5, name is 3,5-Bis(trifluoromethyl)benzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 22227-26-5

General procedure: Benzamide (476 mg, 3.9 mmol) and benzaldehyde(203 mL, 2 mmol) were dissolved in dry DMF (8 mL).TMSCl (507 mL, 4mmol) was added as a catalyst and wasstirred at 50 ¡ãC for 18 h under nitrogen. Awhite precipitatewas formed with the addition of a few drops of water andwas purified by stirring with diethyl ether for 30 min. Theproduct was isolated using vacuum filtration. Yield 31percent

The synthetic route of 22227-26-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Clarke, Harriet J.; Van Rossom, Wim; Horton, Peter N.; Light, Mark E.; Gale, Philip A.; Supramolecular Chemistry; vol. 28; 1-2; (2016); p. 10 – 17;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

354-38-1, 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. 354-38-1, name is 2,2,2-Trifluoroacetamide, This compound has unique chemical properties. The synthetic route is as follows.

Prepared from Intermediate 5 by a method analogous to that reported by Bolm et ah, Organic Letters, 2004, 6(8), 1305-1307, using trifluoroacetamide and (diacetoxy- iodo)benzene in the presence of dirhodium tetraacetate. 5H (500 MHz, CDCI3) 8.79 (d, J 1.4 Hz, IH), 8.22-8.19 (m, IH), 8.18 (dd, J8.4, 2.0 Hz, IH), 3.56 (s, 3H).

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; UCB BIOPHARMA SPRL; CHOVATIA, Prafulkumar Tulshibhai; HUTCHINGS, Martin Clive; KROEPLIEN, Boris; REUBERSON, James Thomas; (102 pag.)WO2016/198401; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 621-38-5, name is 3-Bromoacetanilide, 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. 621-38-5

A. 2-Bromo-4-(1-oxoethylamino)-benzenesulfonyl chloride To 2-bromo-4-(1-oxoethylamino)-benzene (6.2 g, 29 mmol) was added chlorosulfonic acid (20 mL). The solution was heated at 57 C. for 3 hours, an additional 10 mL of chlorosulfonic acid was added and the solution was heated at 67 C. for 6 hours. The mixture was added dropwise to ice water and the heterogeneous mixture was extracted with ethyl acetate. The organic extract was washed once with brine, dried (magnesium sulfate) and evaporated. The residue was dissolved in ethyl acetate (50 mL) and the solution was filtered. The insoluble solid was rinsed twice with ethyl acetate and the combined filtrates were evaporated to afford 6.9 g (82%) of crude compound A as a brown foamy gum.

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 621-38-5.

Reference:
Patent; Bristol-Myers Squibb Co.; US5514696; (1996); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 112257-19-9, name is tert-Butyl methyl(2-(methylamino)ethyl)carbamate, I believe this compound will play a more active role in future production and life. 112257-19-9

To a solution of 2 (465mg, 2.66mmol) in CH2Cl2 (20mL) was added 8 (500mg, 2.66mmol) and sodium triacetoxyborohydride (1.13g, 5.32mmol) at 0¡ãC under argon and then stirred at room temperature for 12h. The reaction solution was quenched with saturated NH4Cl (20mL) and extracted with CH2Cl2 (30mL ¡Á 3), and the combined organic layers dried with Na2SO4. The residue was purified by column chromatography on silica gel using EtOAc/petroleum ether (1/2, V/V) as elunt to give 10 as colorless oil (750mg, 81percent); 1H NMR (400MHz, DMSO) delta 6.49 (d, J = 3.2Hz, 1H, Ar-H), 6.35 (d, J = 3.2Hz, 1H, Ar-H), 3.52 (s, 2H, CH2), 3.29-3.20 (m, 2H, CH2), 2.76 (d, J = 9.8Hz, 3H, CH3), 2.42 (t, J = 6.7Hz, 2H, CH2), 2.18 (s, 3H, CH3), 1.45 (s, 9H, (CH3)3); HRMS (ESI) m/z [M+H]+ Calcd for C14H24BrN2O3+: 347.0970. Found: 347.0974.

The chemical industry reduces the impact on the environment during synthesis 112257-19-9. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yang, Hao; Ouyang, Yifan; Ma, Hao; Cong, Hui; Zhuang, Chunlin; Lok, Wun-Taai; Wang, Zhe; Zhu, Xuanli; Sun, Yutong; Hong, Wei; Wang, Hao; Bioorganic and Medicinal Chemistry Letters; vol. 27; 20; (2017); p. 4635 – 4642;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common heterocyclic compound, 141449-85-6, name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, molecular formula is C11H20N2O2, 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. 141449-85-6.

The 5 – chloro – 1, 6 – naphthyridine (0.93 g, 5 . 65 mmol), hexahydro-pyrrolo [3, 4 – c] pyrrole -2 (1 H) – formic acid tert-butyl ester (1.00 g, 4 . 71 mmol), three (dibenzylidene acetone) two palladium (0.43 g, 0 . 47 mmol), 2 – dicyclohexyl phosphorus – 2, 4, 6 – triisopropyl biphenyl (0.46 g, 0 . 94 mmol), sodium tertiary butyl alcohol (1.40 g, 14.1 mmol) and toluene (20 ml) are added to the 100 ml single-port in the bottle, under the protection of nitrogen, reaction temperature to 120 C reaction 36 hours. Stopping the reaction, the reaction solution is distilled under reduced pressure to remove the solvent after purification by silica gel column chromatography (petroleum ether/ethyl acetate (v/v)=1/1) to obtain the title compound (light yellow liquid, 1.15 g, 71.7%).

The synthetic route of tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Zhang Yingjun; Xue Yaping; Lao Jinhua; Nie Biao; Xu Juan; (35 pag.)CN107759620; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics