Tag: M.W=100-200

These common heterocyclic compound, 518057-72-2, name is 5-Amino-2-fluorobenzamide, 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. category: amides-buliding-blocks

To a solution of 5-amino-2-fluoro-benzamide (0.88 g, 5.7 mmol) and DIEA (3.0 mL, 17 mmol) in THF (20 mL) and dichloromethane (10 mL) at 0 C was added a solution of 6-cyclopropyl-4- [2-methoxy-4-(trifluoromethoxy)phenoxy]pyridine-3-carbonyl chloride (2.1 g, 5.4 mmol) in dichloromethane. The reaction mixture was removed from the ice bath and stirred at room temperature for 1 hour. The reaction mixture was diluted with water and extracted with dichloromethane. The organic layer was concentrated in vacuo and the resulting solid was purified using silica gel chromatography (0-60% ethyl acetate/hexanes) to provide N-(3 -carbamoyl -4-fluoro-phenyl)-6- cyclopropyl-4-[2-methoxy-4-(trifluoromethoxy)phenoxy]pyridine-3-carboxamide (1.1 g, 40%). ESI-MS m/z calc. 505.13, found 506.2 (M+l)+; retention time (Method B): 1.4 minutes (3 minute run). ‘H NMR (400 MHz, DMSO-d6) delta 10.41 (s, 1H), 8.55 (s, 1H), 7.99 (dd, J = 6.5, 2.8 Hz, 1H), 7.87 – 7.76 (m, 1H), 7.69 (d, J = 14.5 Hz, 2H), 7.45 (d, J = 8.8 Hz, 1H), 7.32 – 7.18 (m, 2H), 7.07 (ddd, J = 8.8, 2.8, 1.3 Hz, 1H), 6.59 (s, 1H), 3.80 (s, 3H), 2.07 (p, J = 6.7 Hz, 1H), 0.99 – 0.87 (m, 4H) ppm.

The synthetic route of 5-Amino-2-fluorobenzamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; AHMAD, Nadia; ANDERSON, Corey; ARUMUGAM, Vijayalaksmi; ASGIAN, Iuliana, Luci; CAMP, Joanne, Louise; FANNING, Lev Tyler, Dewey; HADIDA RUAH, Sara, Sabina; HURLEY, Dennis; SCHMIDT, Yvonne; SHAW, David; SHETH, Urvi, Jagdishbhai; THOMSON, Stephen, Andrew; (691 pag.)WO2019/14352; (2019); A1;,
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These common heterocyclic compound, 78191-00-1, name is N-Methoxy-N-methylacetamide, 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. name: N-Methoxy-N-methylacetamide

4-Prop-2-ynyl-morpholine (22 g, 176 mmol) was dissolved under nitrogen in THF (40 mL) and cooled to-40 C. Then a 2 M solution of isopropyl magnesium chloride in THF (97 mL, 193 mmol) was added while keeping the temperature below-20 C. Stirring at – 40 C to-30 C was continued for 30 min. In a separate flask, N-methoxy-N- methylacetamide (20 g, 193 mmol) was dissolved under nitrogen in THF (40 mL) and cooled to-10 C in ice/MeOH. The Grignard solution prepared above was transferred to the Weinreb amide solution at-10 C via teflon tubing under slightly positive nitrogen pressure in vessel 1. There was no exotherm. Stirring at-10 C to 0 C was continued for 2 h. Ther resulting white suspension was poured on a 1 : 1-mixture of ice and saturated NH4Cl solution (400 mL). Extraction: 2 x AcOEt, 1 x saturated NaCl solution. One obtained a yellow oil (26. 1 g, 89 %). Chromatography on silica gel in heptane/ethyl acetate 1: 2 gave 19.4 g (66 %) of a brown oil which was distilled in the Kugelrohr at 130 C/0. 2 mbar. One obtained 15.8 g (53 %) of a yellow oil.

The synthetic route of N-Methoxy-N-methylacetamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2005/94828; (2005); 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. 78888-18-3, name is tert-Butyl allylcarbamate, A new synthetic method of this compound is introduced below., Application In Synthesis of tert-Butyl allylcarbamate

Tert-butyl N-(2-oxiranylmethyl)carbamate was synthesized according to the method of Rocheblave (30). 1 g (6 mmol, 1 equiv) of N-t-BOC protected 3 was dissolved in 50 mL dry CH2Cl2. The solution was brought to 0 C. and kept cold upon addition or 2.8 g (12 mmol, 2 equiv) MCPBA. The solution was then brought to room temperature and stirred overnight.About half of the reaction mixture was taken and diluted with additional 80 mL of CH2Cl2. The solution was washed with 10% Na2SO3, followed by washing with saturated NaHCO3 3 times, and finally by washing with water. The organic layer was dried over Na2SO4 and concentrated in vacuo, yielding crude epoxide 4. By 1H NMR, approximately 85% yield was achieved.1H NMR (400 MHz, CDCl3): delta 1.44 (s, 9H), 2.59-2.78 (brm, 2H), 3.04-3.54 (m, 3H), 4.75 (brs, 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; University of Southern California; US2008/312440; (2008); A1;,
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Reference of 1882-71-9,Some common heterocyclic compound, 1882-71-9, name is 2-Amino-5-methoxybenzamide, molecular formula is C8H10N2O2, 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: A mixture of 2-aminobenzamide (1, 4.0 mmol), carboxamide (2, 6.0 mmol), Yb(OTf)3 (0.20 mmol,5.0 molpercent), and mesitylene (5.0 mL) was placed in a 20-mL Pyrex flask equipped with a magnetic stirring bar and a reflux condenser under a flow of argon. The reaction was carried out at 120-165 oC (bath temp.) for 6 h with stirring. Then, the reaction mixture was cooled to room temperature, and analyzed by GLC, GC-MS (EI), and LC-MS (ESI). After evaporation of mesitylene under vacuum,the products (3) were isolated by recrystallization from MeOH/hexane and/or medium pressure column chromatography on silica gel (eluent: EtOAc/hexane = 50/50 ~ EtOAc 100percent. For 3j, eluent:MeOH/CHCl3 = 50/50). 1H NMR spectra were recorded at 400 MHz, and 13C NMR spectra wererecorded at 100 MHz in DMSO-d6. The analytical and spectral data of 3a-e,38 3f,39 3g,40 3h,41 and3j,42 were consistent with those reported previously. The product, 3i, was characterized below.

The synthetic route of 1882-71-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yoshimura, Tsutomu; Yuanjun, Di; Kimura, Yu; Yamada, Hisatsugu; Toshimitsu, Akio; Kondo, Teruyuki; Heterocycles; vol. 90; 2; (2015); p. 857 – 865;,
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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. 960234-99-5, name is 3-Amino-5-methoxybenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Amino-5-methoxybenzamide

General procedure: 3-aminobenzamide (50 mg, 0.37 mmol) and maleic anhydride (43.2 mg, 0.44 mmol) were dissolved in dry THF (1 ml) and stirred at room temperature for 18 hours. The precipitate was filtered off and dried in vacuo to give 2 (71 mg, 83%).

The synthetic route of 960234-99-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ekblad, Torun; Lindgren, Anders E.G.; Andersson, C. David; Caraballo, Remi; Thorsell, Ann-Gerd; Karlberg, Tobias; Spjut, Sara; Linusson, Anna; Schueler, Herwig; Elofsson, Mikael; European Journal of Medicinal Chemistry; vol. 95; (2015); p. 546 – 551;,
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Adding a certain compound to certain chemical reactions, such as: 19047-31-5, name is 2-Chloro-N-cyclopropylacetamide, 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 19047-31-5, Computed Properties of C5H8ClNO

Compound 1d (30 mg, 0.13 mmol) was dissolved in 2 mL of DMF,Potassium carbonate (37.0 mg, 0.27 mmol) was added,80 reaction 30min,Compound 2a (26.8 mg, 0.20 mmol) was added,80 C overnight.After the reaction is over,Cool to room temperature.Add appropriate amount of water,Ethyl acetate was extracted three times,The organic phases were combined and washed with saturated brine,Dried over anhydrous magnesium sulfate,The crude product was distilled under reduced pressure.Separation and purification by column chromatography,A 33.6 mg white solid was obtained.Yield: 78.1%

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-Chloro-N-cyclopropylacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang University; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; Chen, Jianzhong; Xie, Xin; Qian, Haiyan; Chen, Lili; Wang, Zhilong; (42 pag.)CN106167497; (2016); A;,
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Related Products of 2603-10-3, 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 2603-10-3 as follows.

7.5 g methyl phenyl carbamate (MPC) was added to 50 mL single-necked flask, 20 mL of dimethyl carbonate was added, heated at 60 and dissolved. 10 mL of concentrated hydrochloric acid (37% w / w) was added, 10mL formaldehyde solution (mass concentration of 36%), was added and reacted for two hours. After the reaction was completed, the solid was filtered, the filtrate was analyzed by high performance liquid chromatography, the contents of phenyl carbamate and diphenylmethane dicarbamate (MDC) were determined. The solid was washed three times with 50 ml of water, vacuum dried at 80 for 48h. A small amount of solid samples were taken and content and purity of diphenylmethane dicarbamate were determined. Analysis results showed that MPC conversion was 99%, MDC yield was 97% and selectivity was 98%.

According to the analysis of related databases, 2603-10-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sinopec Corporation; Nan Hua Group Institute; Ding Hongxia; Jin Yucun; Jin Hanqiang; Wu Qijian; Chen Yongping; Liu Zhuo; He Yumiao; (7 pag.)CN107434774; (2017); A;,
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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. 96-30-0, name is 2-Chloro-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 96-30-0

Step B 2-[[2-(3-Benzyloxy-phenyl)-ethyl]-(cyclopropylmethyl)amino]-N-methyl-acetamide hydrochloride; A mixture of 0.24 g (0.85 mmol) of [2-(3-benzyloxy-phenyl)-ethyl]- (cyclopropylmethyl)amine, 0.14 ml (1.00 mmol) of triethylamine, 0.11 g (1.02 mmol) of 2- chloro-N-methyl-acetamide in 3 ml of dimethylformamide was heated with microwaves to 120 0C for 2 hours. The solvent was removed and the crude residue was purified by flash chromatography (dichloromethane/methanol/Ntb 100:0:0 -? 95:5:0.5 gradient). The product obtained was dissolved in anhydrous hydrochloric acid in ethyl acetate, the solvent was removed under vacuum and the residue was triturated with diethyl ether. 0.24 g (80% yield) of the title compound was isolated as a yellow solid.1H-NMR CDCl3: 7.47-6.68 (m, 9H); 5.06 (s, 2H); 3.15 (s, 2H); 2.86-2.62 (m, 4H); 2.56 (d, 3H); 2.43 (d, 2H); 0.92 -0.67 (m, IH); 0.59 -0.44 (m, 2H); 0.16 -0.04 (m, 2H) LC-MS: MH+ = 353

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 96-30-0.

Reference:
Patent; NEWRON PHARMACEUTICALS S.P.A.; WO2007/71311; (2007); A1;,
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These common heterocyclic compound, 154350-29-5, name is Cyclopropanesulfonamide, 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. Safety of Cyclopropanesulfonamide

14-tert-Butoxycarbonylamino- 18-(tert-butyl-dimethyl-silanyloxy)-2, 15-dioxo-3, 16- diaza-tricyclo[14.3.0.04’6]nonadec-7-ene-4-carboxylic acid (500 mg, 0.86 mmoL) was dissolved in 25 mL of THF and treated with CDI (180 mg, 1.12 mmoL). (Care was taken to avoid moisture by using oven dried glassware and maintaining a dry N2 atmosphere). After refluxing the reaction mixture for 2 h, it was cooled to rt and treated sequentially with cyclopropylsulfonamide (135 mg, 1.12 mmoL) and DBU (170 mg, 1.12 mmoL). The reaction mixture was stirred for 4 h at rt, and the THF was removed by rotary evaporation. The residue was partitioned between ethyl acetate and pH 4 buffer. The organic phase was dried (MgSO4) and concentrated in vacuo to give the crude product. It was then purified by flash chromatography (eluting with 33percent ethyl acetate in hexane) to give 300 mg (51percent) of [ 18-(tert-butyl- dimethyl-silanyloxy)-4-cyclopropanesulfonylaminocarbonyl-2,15-dioxo-3,16-diaza- tricyclo[14.3.0.04’6]nonadec-7-en-14-yl]-carbamic acid tert-butyl ester as a white solid. 1H NMR (300 MHz, CD3OD) delta IH 0.07 (s, 3 H), 0.08 (s, 3 H), 0.85 (s, 9 H), 0.87-1.49 (m, 21 H), 1.73-1.95 (m, 3 H), 2.08-2.16 (m, 1 H), 2.25-2.36 (m, 2 H), 2.42-2.56 (m, 1 H), 2.85-2.93 (m, 1 H), 3.65-3.74(dd, ./=10.61, 3.66 Hz, 1 H), 3.89 (d, J=10.25 Hz, 1 H), 4.34 (m, J=9.70, 9.70 Hz, 1 H), 4.43 (t, J=7.87 Hz, 1 H), 4.57 (s, 1 H), 4.94-5.01 (m, 1 H), 5.10 (d, J=8.78 Hz, 1 H), 5.66-5.75 (m, 1 H), 6.55 (s, 1 H), 10.13 (s, 1 H); MS m/z 683 (M++l).

The synthetic route of Cyclopropanesulfonamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/64057; (2008); A1;,
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1943-79-9, name is Phenyl methylcarbamate, 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: Phenyl methylcarbamate

To a solution of amine 11 (0.8 g, 3.35 mmol) in 20 mL of DMSO,were added N-methylphenylcarbamate (0.76 g, 5.03 mmol) andtriethylamine (0.7 mL, 5.03 mmol). The mixture was stirred andheated at 60 C for 3 h, then hydrolyzed and extracted with CH2Cl2.The organic layer was washed with an aqueous solution of 1 M HCland water, dried over MgSO4, filtered and concentrated underreduced pressure. The obtained product was then purified by flashchromatography using a mixture of cyclohexane/ethyl acetate(8:2). Recrystallization from toluene gave 11f as a white solid (45%yield); Mp 142-144 C; 1H NMR (300 MHz, CDCl3): delta 7.98 (d, 1H,8.7 Hz), 7.62 (dd, 1H, 7.8 Hz and 1.2 Hz), 7.51 (dd, 1H, 7.8 Hz and1.2 Hz), 7.32 (t, 1H, 7.8 Hz), 6.92 (d, 1H, 8.7 Hz), 4.80 (br s, 1H), 4.23(br s, 1H), 4.09 (s, 3H), 3.60 (q, 2H, 6.6 Hz), 3.38 (t, 2H, 6.6 Hz), 2.67(d, 3H, 4.8 Hz); 13C NMR (75 MHz, CDCl3): delta 161.7,159.1,145.0,139.3,136.1, 130.2, 126.3, 125.1, 123.9, 112.7, 53.4, 41.6, 32.0, 27.1; IR (upsilon,cm-1, KBr): 3368 (NH), 3291 (NH), 1653 (C=O); MS (APCI, pos. 30V) m/z: [M+H]+, 260.30. HRMS (ESI+): m/z = calcd. for C14H17N3O2[M+H]+ 260.13935 found: 260.13831.

The synthetic route of 1943-79-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Landagaray, Elodie; Ettaoussi, Mohamed; Rami, Marouan; Boutin, Jean A.; Caignard, Daniel-Henri; Delagrange, Philippe; Melnyk, Patricia; Berthelot, Pascal; Yous, Said; European Journal of Medicinal Chemistry; vol. 127; (2017); p. 621 – 631;,
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