Month: January 2021

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);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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;,
Amide – Wikipedia,
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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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 89976-75-0, name is 6-Amino-2H-1,4-benzoxazin-3(4H)-one, 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. COA of Formula: C8H8N2O2

B. To a solution of 1-phenyl-piperidine-4-carboxylic acid (0.03 g, 0.122 mmol) in 5 mL of CH2Cl2 was added oxalyl chloride (0.02 mL, 0.244 mmol) and a catalytic amount of DMF. The reaction mixture was stirred for 2 hours. Solvent was evaporated to dryness under reduced pressure. The residue was redissolved in 5 mL of CH2Cl2. 6-amino-2H-1,4-benzoxazine-3(4H)-one (0.02 g, 0.122 mmol) and triethylamine (0.03 mL, 0.183 mmol) were added sequentially into the acyl chloride solution at 0¡ã C. The reaction mixture was warmed to 25¡ã C. and stirred for 20 min. Concentration of the solvent provided the residue which was then purified by flash column chromatography with hexanes and ethyl acetate to afford 1-phenyl-piperidine-4-carboxylic acid (3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-amide as white solid. 1H NMR (400 MHz, CD3OD) delta (ppm): 7.61-7.58 (m, 4H), 7.54-7.51 (m, 1H), 7.39 (t, 1H), 7.04-7.01 (m, 1H), 6.91 (d, 1H), 4.54 (s, 2H), 3.84 (d, 2H), 3.66-3.59 (m, 2H), 2.82-2.79 (m, 1H), 2.28-2.23 (m, 4H). Mass Spectrum (LCMS, ESI pos.) Calcd. for C20H21N3O3: 351.4. Found: 352.1 (M++1).

The synthetic route of 6-Amino-2H-1,4-benzoxazin-3(4H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Calvo, Raul R.; Cheung, Wing S.; Player, Mark R.; US2006/116368; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 1268810-09-8,Some common heterocyclic compound, 1268810-09-8, name is tert-Butyl (1-ethynylcyclopropyl)carbamate, molecular formula is C10H15NO2, 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 (1-ethynylcyclopropyl)carbamate (200.0 mg, 1.104 mmol) was treated with azidotrimethylsilane (508.6 mg, 4.414 mmol, 4 equiv.) in the presence of copper iodide (21.0 mg, 0.11 mmol) inN,N-dimethylformamide (1 mL) and methanol (1 mL) and stirred at 110 C for 2 h. After cooling, purification by prep HPLC (Phenomenex Luna C18 column, 5% to 100% gradient acetonitrile in water with 0.1% TFA) gave tert-butyl (1-(1H- 1 ,2,3-triazol-4-yl)cyclopropyl)carbamate. LCMS-ESI+ (mlz): [M+Hj + calculated for C10H17N402: 225.1; found: 225.1.

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 (1-ethynylcyclopropyl)carbamate, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; DU, Jinfa; KAPLAN, Joshua A.; KIRSCHBERG, Thorsten A.; KOBAYASHI, Tetsuya; LAZERWITH, Scott E.; LEE, Rick Andrew; MEDLEY, Jonathan William; MITCHELL, Michael L.; MORGANELLI, Philip Anthony; PYUN, Hyung-Jung; SHEVICK, Sophia L.; SQUIRES, Neil H.; WATKINS, William J.; (294 pag.)WO2018/39531; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 698-67-9, These common heterocyclic compound, 698-67-9, name is 4-Bromobenzamide, 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 Schlenk tube was charged with Cu2O (7.2 mg, 10 molpercent), l-proline (11.5 mg, 20 molpercent), aryl (or heteroaryl) bromide (1 or 3,0.50 mmol), potassium iodide (KI) (249 mg, 0.75 mmol), and EtOH(1.5 mL) under nitrogen atmosphere. The Schlenk tube was sealedwith a teflon valve, and then the reaction mixture was stirred at110C for a period (the reaction progress was monitored by GCanalysis). After the reaction was completed, GC yield of high volatileproduct was determined using an appropriate internal standard(chlorobenzene or 1-chloro-4-methylbenzene) or the solvent wasremoved under reduced pressure. The residue obtained was puri-fied via silica gel chromatography (eluent: petroleum ether/ethylacetate = 10/1) to afford aryl iodides 2a?2o or heteroaryl iodides4a?4g.

Statistics shows that 4-Bromobenzamide is playing an increasingly important role. we look forward to future research findings about 698-67-9.

Reference:
Article; Feng, Xiujuan; Li, Lingyu; Yu, Xiaoqiang; Yamamoto, Yoshinori; Bao, Ming; Catalysis Today; vol. 274; (2016); p. 129 – 132;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics