Amides-buliding-blocks

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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Related Products of 42137-88-2,Some common heterocyclic compound, 42137-88-2, name is N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide, molecular formula is C11H15Cl2NO2S, 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 suspension of N-(4-(aminomethyl)-3-(trifluoromethyl)phenyl)-3-(imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methylbenzamide (If) (3.22 g, 7.18 mmol) in diisopropylethylamine (2.49 mL, 14.32 mmol) was charged N,N-bis(2-chloroethyl)-4-toluenesulfonamide (2.13 g, 7.18 mmol). The reaction mixture was heated to reflux (-130 C.) for 36 h. The progress of the reaction was monitored by TLC. The reaction mixture was transferred into a mixture of deionized water (6 mL), ice (20 g), potassium carbonate (7 g), and dichloromethane (25 mL). The layers were separated and the aqueous layer extracted with dichloromethane (3*5 mL). The combined organic layers were treated with activated charcoal, dried over magnesium sulfate, and then evaporated to dryness under vacuum to give the product 3-(imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-(4-((4-tosylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide (Ig) (2.2 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide, its application will become more common.

Reference:
Patent; Apicore, LLC; Kovi, Ravishanker; Kannapan, Jayaraman; Thakor, Sanjay F.; Patel, Rajesh A; US2014/343282; (2014); A1;,
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Electric Literature of 191170-76-0,Some common heterocyclic compound, 191170-76-0, name is Benzyl 4-bromophenethylcarbamate, molecular formula is C16H16BrNO2, 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 solution of intermediate 3.3 (2g, 6 mmol, 1 eq.) and intermediate 3.10 (2g, 6 mmol, 1 eq.) in DMF is purged with Ar2 for 10 min. Pd(dppf)Cl2 (122 mg, 0.15 mmol, 0.4 eq.) and 8 mL 2N Na2Ctheta3/H2O are then added and the resulting reaction mixture is sealed in a tube and heated to 120 0C in a microwave oven for 30 min. The reaction mixture is diluted with EtOAc and washed with water and brine. The organic layer is dried over Na2SO4, filtered and concentrated to give a dark oil that is purified by flash column (40%~60% EtOAc/hexanes, 40 g column) yielding intermediate 3.11 as a light greenish oil (2 g, 4.3 mmol, 72%).

The synthetic route of 191170-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/52078; (2009); A1;,
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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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Some common heterocyclic compound, 185693-02-1, name is tert-Butyl hexahydropyrrolo[3,4-b]pyrrole-1(2H)-carboxylate, molecular formula is C11H20N2O2, 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. Formula: C11H20N2O2

The product from Step 2 (150mg, 0.5mmol), tert-butyl hexahydropyrrolo[3,4-b]pyrrole-1-carboxylate (100mg, 0.5mmol), and anhydrous potassium carbonate (128mg, 0.9mmol) were suspended in N,N-dimethylformamide (3.0mL). The mixture was reacted at 80C for 1h. The reaction mixture was poured into 20ml ice water, and extracted with ethyl acetate. The organic phases were combined, washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated under reduced pressure to remove the solvent to produce a crude product. The crude product was purified with a silica gel column chromatography to produce the title compound (110mg). ESI-MS (m/z): 455.2 [M + H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 185693-02-1, its application will become more common.

Reference:
Patent; Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd.; CAI, Jiaqiang; YU, Nan; ZENG, Hong; SONG, Hongmei; QING, Yan; SONG, Shuai; DENG, Hanwen; TANG, Zujian; DUAN, Xiaofan; HUANG, Haitao; YE, Hong; LIU, Gang; WANG, Lichun; WANG, Jingyi; (81 pag.)EP3511332; (2019); A1;,
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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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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;,
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