Tag: M.W=100-200

Application of 67442-07-3, A common heterocyclic compound, 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, molecular formula is C4H8ClNO2, 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.

Under nitrogen protection, 1340.5g of intermediate was taken, dissolved in 200mL anhydrous THF, the reaction system was cooled to -15¡ã, and 13g of THF solution of 13g isopropylmagnesium chloride was added dropwise. During the dropwise addition, the reaction temperature was controlled at -5¡ã. After the completion of the dropwise addition, the reaction was continued for 1 h, and then 60 g of a solution of 15 g of 2-chloro-N-methoxy-N-methylacetamide in THF was added dropwise thereto, and the reaction temperature was controlled not to exceed -5¡ã during the dropwise addition. After the end of the addition, the temperature of the system was raised to -5-0 ¡ã, and after the reaction was completed, the reaction was quenched by the addition of 2N hydrochloric acid at 0 ¡ã, and ethyl acetate (200 mL) was added, and the mixture was separated. , filtration, solvent recovery under reduced pressure, residue,With methanol:Water = 10:1 recrystallized to give a white solid, 27 g, yield 76percent.

The synthetic route of 67442-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Engineering Polytechnic College; Feng Chengliang; Yao Wenjin; Yan Bin; (12 pag.)CN109678686; (2019); A;,
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Application of 41921-63-5,Some common heterocyclic compound, 41921-63-5, name is 4,5-Dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one, molecular formula is C9H10N2O, 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.

d) 7-Bromo-1 ,3,4,5-tetrahydro-2H-1 ,3-benzodiazepin-2-one.To a solution of 1 ,3,4,5-tetrahydro-2H-1 ,3-benzodiazepin-2-one (55 mg, 0.340 mmol) in dry dimethylformamide (3 mL) was added N-bromosuccinimide (67 mg, 0.374 mmol) in one portion. After 30 min, the reaction mixture was quenched with water (5 mL) and extracted with three 10 mL portions of ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (7% methanol in dichloromethane) to give 55 mg (67%,) of 7-bromo-1 ,3,4,5-tetrahydro-2H-1 ,3- EPO benzodiazepin-2-one as a white solid. ESMS [M+H]+: 241.0.

The synthetic route of 41921-63-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/113432; (2006); A2;,
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Synthetic Route of 104863-65-2, 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 104863-65-2 as follows.

A solution of 140 mL (0.18 mol) of 1.3M sec-butyl lithium in cyclohexane was added slowly to N-tert-butoxycarbonyl-3-methoxy-2-methylaniline (21.3 g, 0.09 mol) in 250 mL of THF keeping the temperature below -40 C. with a dry ice-ethanol bath. The bath was removed and the temperature allowed to warm to 0 C. and then the bath replaced. After the temperature had cooled to -60 C., 18.5 g (0.18 mol) of N-methoxy-N-methylpropanamide in an equal volume of THF was added dropwise. The reaction mixture was stirred 5 minutes, the cooling bath removed and stirred an additional 18 hours. It was then poured into a mixture of 300 mL of ether and 400 mL of 0.5N HCl. The organic layer was separated, washed with water, brine, dried over MgSO4, and concentrated at reduced pressure to give 25.5 g of a crude of 1-[2-(tert-butoxycarbonylamino)-6-methoxyphenyl]-2-butanone. This material was dissolved in 250 mL of methylene chloride and 50 mL of trifluoroacetic acid and stirred for a total of 17 hours. The mixture was concentrated at reduced pressure and ethyl acetate and water added to the remaining oil. The ethyl acetate was separated, washed with brine, dried (MgSO4) and concentrated. The residue was chromatographed three times on silica eluting with 20% EtOAc/hexane to give 13.9 g of 2-ethyl-4-methoxy-1H-indole.

According to the analysis of related databases, 104863-65-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Harper, Richard Waltz; Lin, Ho-Shen; Richett, Michael Enrico; US2004/29948; (2004); A1;,
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Synthetic Route of 4815-28-5,Some common heterocyclic compound, 4815-28-5, name is 2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, molecular formula is C9H12N2OS, 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 492-(2-(3-(trifluoromethyl)-4,5,6,7-tetrahydroindazole-1-yl)propanamido)-4,5,6,7- tetrahydrobenzorithiophene-3-carboxamide a) 2-(3-chloropropanamido)-4,5,6,7-tetrahydrobenzo[]thiophene-3-carboxamide2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (250 mg, 1.28 mmol) and triethylamine (0.18 ml_, 1.28 mmol) were stirred in DCM (5 ml_). 3-chloropropionylchloride (162 mg, 1.28 mmol) was added dropwise under a nitrogen atmosphere. Stirring was continued for 2 h. 2 M HCI (20 ml_) was added and the reaction mixture extracted into DCM (3 x 50 ml_), The combined DCM layers were washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo to give the desired product as a yellow solid (290 mg, 1.01 mmol, 79 %).1 H NMR (400MHz, CDCI3): delta 1.86 (m, 4H), 2.72 (m,4H), 2.91 (t,2H), 3.86 (t, 2H), 5.73 (s, 2H), 12.1 (s,1 H).

The synthetic route of 4815-28-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. ORGANON; WO2008/3452; (2008); A1;,
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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;,
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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

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