Category: amides-buliding-blocks

518057-72-2, name is 5-Amino-2-fluorobenzamide, 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. COA of Formula: C7H7FN2O

A solution of 5-amino-2-fluoro-benzamide (30 mg, 0.19 mmol) and diisopropylethylamine (100 mu, 0.5766 mmol) in tetrahydrofuran (1 mL) at 0 C was added to a slurry of 2-[2-methoxy-4- (trifluoromethoxy)phenoxy]-5-(l, l,2,2,2-pentafluoroethyl)benzoyl chloride (89 mg, 0.19 mmol) in tetrahydrofuran (1 mL) slowly at 0 C and the reaction was stirred at room temperature for 4 hours. The solvent was evaporated by blowing down with nitrogen. The crude product was dissolved in DMSO, filtered and purified by reverse phase HPLC to yield N-(3-carbamoyl-4-fluoro-phenyl)-2-[2-methoxy-4- (trifluoromethoxy)phenoxy]-5-(l, l,2,2,2-pentafluoroethyl)benzamide (25.7 mg, 23%). ESI-MS m/z calc. 582.08, found 583.0 (M+l)+; retention time (Method B): 2.04 minutes (3 minute run). NMR (400 MHz, DMSO-d6) delta 10.62 (s, 1H), 8.00 (dd, J = 6.5, 2.8 Hz, 1H), 7.91 (d, J = 2.4 Hz, 1H), 7.83 (ddd, J = 9.0, 4.4, 2.8 Hz, 1H), 7.78 – 7.62 (m, 3H), 7.44 (d, J = 8.8 Hz, 1H), 7.32 – 7.24 (m, 2H), 7.07 (ddd, J = 8.8, 2.8, 1.3 Hz, 1H), 6.87 (d, J = 8.8 Hz, 1H), 3.78 (s, 3H) ppm.

The synthetic route of 518057-72-2 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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Application of 79722-21-7, A common heterocyclic compound, 79722-21-7, name is tert-Butyl benzyloxycarbamate, molecular formula is C12H17NO3, 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.

To a solution of N-Boc-benzyloxyamine (2 ¡¤ lg, 9.44 mmol, 1.2 eq) in DMAC (20 ml) was added potassium tert-butoxide (1.06 g, 9.44 mmo 1,1 ¡¤ 2 eq) After 30 min, a solution of compound 8 (4 ¡¤ Og, 7 ¡¤ 87 mmo 1) in DMAC (20 ml) was added and the reaction was quenched at room temperature for 10 h. The reaction was quenched with saturated ammonium chloride solution (30 ml), concentrated, And the aqueous phase was extracted with ethyl acetate (50 ml * 2), washed with saturated brine (20 ml), dried over anhydrous sodium sulfate and concentrated to give compound 9 (3.788, 95%). The 111 bandits 1? (4001 hold, 0) (: 13): 38.01

The synthetic route of 79722-21-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Kaimo Biological Technology Co., Ltd.; Tian Yanli; Li Yang; (14 pag.)CN105061425; (2017); B;,
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Application of 7150-72-3, A common heterocyclic compound, 7150-72-3, name is tert-Butyl vinylcarbamate, molecular formula is C7H13NO2, 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 suspension of tert-butyl N-vinylcarbamate (25.0 g) and Potassium carbonate (49.2 g) in Tetrahydrofuran (262 mL) was cooled to 0-5C. To this mixture was then added a solution of dibromomethanone oxime (39.0 g) in tetrahydrofuran (89.0 mL) at 0-5C and was stirred for one hour. The reaction mixture was then stirred at rt for 3 hours. The mixture was then extracted twice between ethyl acetate and water. The combined organic layers were dried (MgSO4), filtered and evaporated under vacuo to give a 46.1 g of a crude compound.30 g of this crude were stirred with 50 ml of diethylether for 2 hours. The resulting beige suspensionwas filtered, washed with 2x 20 ml of diethylether and 2x 50m1 of pentane then was dried under vacuo to give 26.54 g of a white solid corresponding to the desired tert-butyl N-(3-bromo-4,5-dihydroisoxazol- 5-yl)carbamate. 1H-NMR(CDCI3, 400 MHz, oe in ppm): 1.47 (s, 9 H)2.95(dd, J=18, 4.8 Hz, 1 H)3.49 (dd, J=18, 9.7 Hz, 1 H) 5.42 (br. s., 1 H) 6.15 (br. s., 1 H)

The synthetic route of 7150-72-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; O’SULLIVAN, Anthony, Cornelius; EL QACEMI, Myriem; CASSAYRE, Jerome, Yves; PITTERNA, Thomas; STOLLER, Andre; (137 pag.)WO2017/50921; (2017); A1;,
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Related Products of 63069-49-8, These common heterocyclic compound, 63069-49-8, name is 2-Amino-5-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.

General procedure: A 12mL vial was charged with MCM-41-2P-Pd(OAc)2 (2mol%), 2-aminobenzamide (1mmol), aryl iodide (1mmol) (if solid) and a stirring bar. Then, DMF (2mL), aryl iodide (1mmol) (if liquid) and DBU (2mmol) were injected by syringe under an argon atmosphere. The vial was placed in an alloy plate, which was transferred into a 300mL Parr Instruments 4560 series autoclave under an argon atmosphere. After flushing the autoclave three times with CO, a pressure of 10bar CO was fixed at ambient temperature. The autoclave was heated for 20hat 120C. After completion of the reaction, the autoclave was cooled to room temperature and the pressure was released carefully. The reaction mixture was diluted with ethyl acetate (10mL) and filtered. The palladium catalyst was washed with distilled water (2¡Á5mL) and acetone (2¡Á5mL), and reused in the next run. The filtrate was concentrated in vacuo and the pure product was isolated by either washed with water, ethyl acetate and finally hexane or recrystallization from MeOH.

Statistics shows that 2-Amino-5-fluorobenzamide is playing an increasingly important role. we look forward to future research findings about 63069-49-8.

Reference:
Article; You, Shengyong; Huang, Bin; Yan, Tao; Cai, Mingzhong; Journal of Organometallic Chemistry; vol. 875; (2018); p. 35 – 45;,
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Related Products of 87905-98-4, A common heterocyclic compound, 87905-98-4, name is Benzyl (5-hydroxypentyl)carbamate, molecular formula is C13H19NO3, 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.

<5-4> Preparation of 1-O-(N-Carbobenzoxy-6-Aminopentyl)-2,3,4,6-tetra-O-Benzoyl-D-Glucopyranoside N-carbobenzoxy-6-aminopentanol (0.32 g, 1.35 mmol) and trimethylsilyl trifluoromethanesulfonate (0.25 ml, 1.35 mmol) were dissolved in dichloromethane (10 ml) and cooled to 0 C. To this solution, was added a solution obtained by dissolving the compound obtained in Preparative Example <5-3> (1 g, 1.4 mmol) in dichloromethane (25 ml), and the mixture thus obtained was stirred for 2 hours.After the completion of the reaction, the reaction mixture was filtered through celite. The filtrate thus obtained was washed with saturated aqueous NaHCO3 and aqueous NaCl. The product thus obtained was dried over Na2SO4, concentrated under a reduced pressure, and then purified by column chromatography (ethyl acetate_hexane=1:2) to obtain the title compound as a transparent sticky oil (0.8 g).1H NMR (CDCl3): delta 1.20-1.54 (m, 6H), 2.93-2.95 (d, J=6.1 Hz, 2H), 3.51-3.54 (m, 1H), 3.88-3.95 (m, 1H), 4.10-4.17 (m, 1H, H-5), 4.47 (dd, J=12.2 Hz, 5.0 Hz, 1H, H-6b), 4.63 (d, J=11.9 Hz, 2H, H-6b, NH), 4.81 (d, J=7.7 Hz, 1H, H-1), 5.08 (s, 1H, benzyl), 5.52 (t, J=9.4 Hz, 1H, H-2), 5.68 (t, J=9.7 Hz, 1H, H-4), 5.91 (t, J=9.6 Hz, 1H, H-3), 7.26-8.03 (m, 25H, arom).

The synthetic route of 87905-98-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chung, Sung-Kee; Lee, Woo Sirl; Kim, Boram; Im, Jungkyun; Ghosh, Subhash C.; US2011/224423; (2011); A1;,
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Reference of 104863-65-2,Some common heterocyclic compound, 104863-65-2, name is N-Methoxy-N-methylpropionamide, molecular formula is C5H11NO2, 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.

Example 14: 2-Propionyl-7-(pyridin-3-yl)dimethylhydrazonoyl imidazo[5,1-b]thiazole; A solution of 1.75 g of 2-bromo-7-(pyridin-3-yl)dimethylhydrazonoylimidazo[5,1-b]thiazole in 10 ml of tetrahydrofuran was cooled to -50C under an argon atmosphere, 15.4 ml of a 0.89 M tetrahydrofuran solution of ethylmagnesium bromide was added thereto, and the mixture was stirred for one hr. N-Methyl-N-methoxypropionamide (2.2 ml) was added thereto at -20C, and the mixture was stirred at room temperature for one hr. A 20% aqueous ammonium chloride solution was added to stop the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium bicarbonate solution and saturated brine in that order and was then dried over anhydrous magnesium sulfate. The solvent was removed by evaporation, and the solid was washed with an ethyl acetate : hexane = 2 : 1 solution to give 0.94 g of 2-propionyl-7-(pyridin-3-yl)dimethylhydrazonoylimidazo[5,1-b]thiazole. 1H-NMR (CDCl3) delta: 1.29 (3H, t, J = 7.1 Hz), 2.92 (2H, q, J = 7.1 Hz), 7.31 – 7.35 (1H, m), 7.98 (1H, ddd, J = 1.6, 1.6, 8.2 Hz), 8.87 – 8.88 (1H, m)

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

Reference:
Patent; Meiji Seika Kaisha, Ltd.; EP1582522; (2005); A1;,
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Synthetic Route of 2360-20-5, The chemical industry reduces the impact on the environment during synthesis 2360-20-5, name is 3,4-Diaminobenzenesulfonamide, I believe this compound will play a more active role in future production and life.

General procedure: Benzaldehyde (73 muL, 0.72 mmol, 1 eq) was dissolved in EtOH (2-5 mL), and sodium metabisulfite (205 mg, 1.08 mmol, 1.5 eq) in H2O (1-2 mL) was added in dropwise. The reaction mixture was stirred at rt overnight. Reaction mixture was diluted with EtOH, cooled and formed precipitate was filtered and dried (128 mg). The mixture of this salt (124.6 mg, 0.596 mmol, 1.5 equiv) and 3-amino-4-(methylamino) benzenesulfonamide (3) (80 mg, 0.397 mmol, 1 equiv) in 5 mL DMF was heated at 60? for 6 h. Reaction mixture was diluted with water and formed precipitate was filtered. The crude product was purified by flash chromatography on silica gel (12 g), eluting with a gradient of 0-11% MeOH in DCM to give 4a (74.5 mg, 64.8% yield) as a white powder. Mp 266-268.6 C. 1H NMR (400 MHz, DMSO-d6): delta 3.92 (3H, s), 7.32 (2H, s), 7.58-7.60 (3H, m), 7.76-7.81 (2H, m), 7.85-7.88 (2H, m), 8.14 (1H, s); 13C NMR (100 MHz DMSO-d6): delta 32.05, 111.05, 116.93, 119.93, 128.75, 129.41, 129.48, 130.12, 138.25, 138.45, 141.53, 155.41; HRMS m/z calculated for C14H13N3O2S [M+H]+ 288.0807, found: 288.0794.

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, 3,4-Diaminobenzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cal??kan, Burcu; Banoglu, Erden; Guer Maz, Tu?ce; Nocentini, Alessio; Supuran, Claudiu T.; Uslu, Azize Gizem; Bioorganic Chemistry; vol. 95; (2020);,
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Synthetic Route of 683-57-8, 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. 683-57-8, name is 2-Bromoacetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 3-chiorophenol (2.57 g, 20.0 mmol), 2-bromoacetamide (2.76 g, 20.0 mmol) and K2C03 (5.53 g, 40.0 mmol) in acetone (40 mL) was stirred at 70 C overnight. The mixture was then cooled to rt and filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE / EtOAc (V / V) = 1: 1) to give the title compound as a white solid (3.22 g, 87%).

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-Bromoacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; ZHANG, Jiancun; WANG, Xiaojun; LIN, Runfeng; CAO, Shengtian; WANG, Zhaohe; LI, Jing; WO2014/12360; (2014); A1;,
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Electric Literature of 24310-36-9, 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 24310-36-9 as follows.

Step 5. Preparation of 1, 2,3, 4-Tetrahydro-benzo [b] azepin-5-one. To preheated polyphosphoric acid (PPA, 220 g) at 70-80 C was added 1- (Toluene-4-sulfonyl)-1, 2,3, 4-tetrahydro-benzo [b] azepin-5-one (50.0 g, 0.16 mol). The mixture was stirred for 3.0 h at the same temperature and then poured into ice water. After the pH was adjusted to about 8-9 by adding aq NaOH, the mixture was extracted with ethyl acetate. The organic layer was separated, dried over MgS04, and concentrated. The residue was purified by silica gel column chromatography (eluent, 3: 1 n-hexanes: ethyl acetate) to give 1, 2,3, 4-Tetrahydro-benzo [b] azepin-5-one (22g).

According to the analysis of related databases, 24310-36-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/37796; (2005); A1;,
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Related Products of 713-41-7, 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. 713-41-7, name is 2-Amino-4-(trifluoromethyl)benzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

-(4-Chlorophenyl)-7-trifluoromethyl-3H-quinazolin To a stirred suspension of 2-amino-4-(trifluoromethyl)benzamide (33.6 g, 0.16 mol) in water (750 mL) was added dropwise 4-chlorobenzaldehyde. Iron trichloride hexahydrate (133 g) was then added in portions. The reaction mixture was then heated at reflux for 24 h. After allowing the suspension to cool to room tempera- ture, the precipitate was isolated by vacuum filtration washing with water (3 x 500 mL) and dried under vacuum (10 mbar, 50C). Yield = 50 g, 94%; HPLC-mass spectrometry (LC-MS): 3.7 min, 325 (M+).

The synthetic route of 2-Amino-4-(trifluoromethyl)benzamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; GROss, Steffen; POHLMAN, Matthias; NARINE, Arun; ROSENBAUM, Claudia; DESHMUKH, Prashant; DICKHAUT, Joachim; BANDUR, Nina Gertrud; KOeRBER, Karsten; KAISER, Florian; VON DEYN, Wolfgang; LANGEWALD, Juergen; CULBERTSON, Deborah L.; EBUENGA, Cecille; WO2011/36074; (2011); A1;,
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