Category: amides-buliding-blocks

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. 459817-82-4, name is tert-Butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide, A new synthetic method of this compound is introduced below., Recommanded Product: 459817-82-4

tert-Butyl l,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (2.76 g, 12.37 mmol) was added portionwise to ethyl 4-(2-chloro-5-methylpyrimidin-4-yl)-lH-imidazole-2-carboxylate (Intermediate 23; 3.0 g, 11.25 mmol), K2CO3 (4.66 g, 33.75 mmol) and 18-crown-6 ether (0.595 g, 2.25 mmol) in 1,4-dioxane (60 mL) at 100 C under air. The resulting solution was stirred at 100 C for 2 hours. The mixture was cooled, filtered and the resulting solid was washed with ethyl acetate. The filtrate was then concentrated under reduced pressure. The crude product was purified by flash silica chromatography, elution gradient 25 to 30% EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford ethyl 1 -(2- ((tert-butoxycarbonyl)amino)ethyl)-4-(2-chloro-5-methylpyrimidin-4-yl)-lH-imidazole-2- carboxylate (Intermediate 22; 3.20 g, 69.4%) as a white solid. H NMR (400 MHz, DMSO, 20.2 C) delta 1.25 (9H, s), 1.35 (3H, t), 2.62 (3H, s), 3.35 (2H, dd), 4.37 (2H, q), 4.49 (2H, t), 6.93 (1H, t), 8.18 (1H, s), 8.61 (1H, s). m/z (ES+), [M+H]+ = 410

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; ASTRAZENECA AB; WARD, Richard, Andrew; JONES, Clifford, David; SWALLOW, Steven; GRAHAM, Mark, Andrew; DOBSON, Andrew, Hornby; MCCABE, James, Francis; (223 pag.)WO2017/80979; (2017); A1;,
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Some common heterocyclic compound, 122334-37-6, name is 4-Chloro-N-methoxy-N-methylbenzamide, molecular formula is C9H10ClNO2, 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

Ethyl magnesium bromide (3.0 M in diethyl ether, 21.5 mL, 64.4 mmol) was added via syringe over a few minutes to a clear colorless solution of 5-bromo-1-methyl-1H-imidazole (10.4 g, 64.4 mmol) in THF (100 mL) under a nitrogen atmosphere in an ice bath. A white precipitate formed during the addition. The mixture was removed from the ice bath and was stirred for 20 minutes, then was again cooled in an ice bath before addition of 4-chloro-N-methoxy-N-methylbenzamide (10.7 g, 53.6 mmol, Intermediate 22: step a). The resulting white suspension was stirred overnight at room temperature. The reaction was quenched by addition of saturated aqueous NH4Cl and diluted with water. The mixture was partially concentrated to remove THF and was diluted with DCM. The mixture was acidified to pH 1 with 1 N aqueous HCl, then neutralized with saturated aqueous NaHCO3. The phases were separated and the aqueous phase was further extracted with DCM. The organic extracts were washed with water, then were dried (Na2SO4), filtered, and concentrated, affording a white solid. The crude product was triturated with a mixture of EtOAc:heptanes (1:1, 150 mL). The precipitated solid was collected by vacuum filtration, washing with heptanes, to afford the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 122334-37-6, its application will become more common.

Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
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Electric Literature of 98-64-6, 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. 98-64-6, name is 4-Chlorobenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 2.2 General procedure: 4-methyl-N-phenylbenzenesulfonamide (3a) A 25 mL oven-dried reaction vessel was charged with Pd(TFA)2 (2.3 mg, 0.01 mmol), 1,10-phenanthroline (3.6 mg, 0.02 mmol), p-toluene sulfonamide (1a, 34.2 mg, 0.2 mmol), cyclohexanone (2a, 32 muL, 0.3 mmol). The reaction vessel was flushed with oxygen three times and then sealed. Toluene (0.7 mL) was added by syringe and the resulting solution was stirred at 140 ¡ãC for 40 h. After cooling to room temperature, the volatiles were removed under vacuum and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 4:1) to give the corresponding product 3a (39.9 mg) as white solid in 81percent yield.

The chemical industry reduces the impact on the environment during synthesis 4-Chlorobenzenesulfonamide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Cao, Xiangxiang; Bai, Yang; Xie, Yanjun; Deng, Guo-Jun; Journal of Molecular Catalysis A: Chemical; vol. 383-384; (2014); p. 94 – 100;,
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Reference of 6973-09-7, A common heterocyclic compound, 6973-09-7, name is 5-Amino-2-methylbenzenesulfonamide, molecular formula is C7H10N2O2S, 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.

Example No.B.1.1 : ter*-Butyl-cis-4-((6-(4-methyl-3-sulf amoylphenylamino)- l/ -p r azolo [3,4- i/|pyrimidin-l-yl)methyl)cyclohexylcarbamate; A solution of ~er~-butyl-cw-4-((6-chloro-l//-pyrazolo[3,4-i/]pyrimidin-l- yl)methyl)cyclohexylcarbamate (1.66 g, 4.53 mmol, prepared using A from Preparation No.2 and ter^butyl-czs-(4-hydroxymethyl)cyclohexylcarbamate [AMRI]), 5-amino-2- methylbenzenesulfonamide (1.10 g, 5.89 mmol, Waterstone), and sodium teri-butoxide (1.306 g, 13.59 mmol) in 1,4-dioxane (15 mL) was stirred at ambient temperature for about 30 min. In a separate 10 mL nitrogen purged vial charged with Pd2(dibenzylideneacetone)3 (0.415 g, 0.453 mmol) and 2-di-~er~-butylphosphino-2′,4′,6′-triisopropylbiphenyl (0.789 g, 1.86 mmol) was added 1,4-dioxane (2 mL) followed by heating to about 80 ¡ãC for about 2 min. The mixture was subsequently cooled to ambient temperature. The catalyst solution was added to the reaction mixture at ambient temperature and the reaction mixture was heated to about 80 ¡ãC for about 16 h. The reaction mixture was cooled to ambient temperature then water (100 mL) and EtOAc (50 mL) were added and the organic layer was separated. The aqueous layer was further extracted with EtOAc (2 x 50 mL) and the combined organic extracts were dried over anhydrous MgSOt, filtered through a silica gel pad, and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography eluting with 50percent EtOAc in heptane to provide tert-butyl-cis-4-((6- (4-methyl-3-sulfamoylphenylamino)-lH-pyrazolo[3,4-d]pyrimidin-l- yljmethyljcyclohexylcarbamate (0.58 g, 25percento) as a light yellow solid. LC/MS (Table 2, Method a) R, = 1.38 min; MS m/z: 516 (M+H)+.

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; ABBOTT LABORATORIES; WOLLER, Kevin R.; CURTIN, Michael L.; FRANK, Kristine E.; JOSEPHSOHN, Nathan S.; LI, Biqin C.; WISHART, Neil; WO2011/156698; (2011); A2;,
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Synthetic Route of 99733-18-3,Some common heterocyclic compound, 99733-18-3, name is tert-Butyl (7-aminoheptyl)carbamate, molecular formula is C12H26N2O2, 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: tert-butyl(3-aminopropyl)carbamate (3a,508 mg, 2.93 mmol)was added toa stirred solutionof4-aminobenzoic acid (2a, 200 mg, 1.46 mmol), EDCI (421mg, 2.20 mmol), HOBt(237 mg, 1.76 mmol), DIEA (502 muL, 2.92 mmol) in DMF (10 mL), stirred overnight at RT. After monitored by TLC to observe completion of reaction, the mixture was diluted with water (20 mL), and then the water phase was extracted with ethylacetate (20 mL¡Á2). The combined organic phase was washed with water (20 mL¡Á3)for three times and dried with anhydrous Na2SO4. The crude product was purified bysilica gel column chromatography to afford intermediates 5aa in 81% yield as whitesolid.

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 (7-aminoheptyl)carbamate, its application will become more common.

Reference:
Article; Wang, Xin; Yu, Chenhua; Wang, Cheng; Ma, Yakun; Wang, Tianqi; Li, Yao; Huang, Zhi; Zhou, Manqian; Sun, Peiqing; Zheng, Jianyu; Yang, Shengyong; Fan, Yan; Xiang, Rong; European Journal of Medicinal Chemistry; vol. 181; (2019);,
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Electric Literature of 115643-59-9, 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. 115643-59-9, name is 2-Amino-6-fluorobenzamide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Compound 14 was prepared according tothe procedure previously reported.38 A solution of sodiumnitrite (4.14 g, 60 mmol) in 0.5 N HCl (240 mL) was stirred at0 C for 20 min. Anthranilamide 13 (30 mmol) dissolved inN,N-dimethylformamide (DMF, 15 mL) was then addeddropwise to the solution described above for 40 min. Afterthe mixture had been stirred for an additional 1 h at 0 C, 30%aqueous ammonia was added slowly to adjust the pH to 10.0.The reaction mixture was allowed to stir for 15 min and thenreacidified to pH 2.0. After the mixture had been stirred for 30min, the precipitated product was filtered off with suction,washed with water (200 mL), and dried to afford compound 14in yields of 75-83%.

The chemical industry reduces the impact on the environment during synthesis 2-Amino-6-fluorobenzamide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhou, Yuan; Feng, Jiangtao; He, Hongwu; Hou, Leifeng; Jiang, Wen; Xie, Dan; Feng, Lingling; Cai, Meng; Peng, Hao; Biochemistry; vol. 56; 49; (2017); p. 6491 – 6502;,
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Electric Literature of 57957-24-1, 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. 57957-24-1, name is N-(1-Phenylvinyl)acetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

; (Examples 10 to 22); In a 50-mL autoclave, 6 mg (1.0¡Á10-2 mmol) of the [rhodium(I)((1S,1S’,2R,2R’)-1,1′-do-tert-butyl-[2,2′]-diphosphetane)(norbornadiene)]hexafluorophosphate synthesized in Example 8 and used as a catalyst and 1 mmol of the dehydroamino acid derivative (or enamide derivative) shown in Table 1 were charged. Then, the system was evacuated and purged with hydrogen four times. The autoclave was returned to normal pressure, and a cock was opened to rapidly add 4 mL of degassed dehydrated methanol from the cock using a syringe and then closed. The reactor was cooled with dry ice/ethanol, and then the reaction system was again evacuated and purged with hydrogen four times. After the hydrogen pressure was set to a predetermined value, the refrigerant was removed, and the reaction system was stirred with a magnetic stirrer until hydrogen consumption was stopped. After the completion of reaction, the reaction solution was passed through silica gel column chromatography (developing solvent: ethyl acetate) to remove the catalyst, and then the residue was concentrated with an evaporator to obtain a reduced product. In any reaction, the yield was about 100%. The optical purity (ee) of each product was analyzed with chiral HPLC or chiral GC. The results are shown in Table 1. These results were obtained at a ratio of substrate : catalyst = 100 : 1. [Table 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, N-(1-Phenylvinyl)acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 143557-91-9, These common heterocyclic compound, 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, 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.

[0178] A reaction flask was charged with crude compound 2 (5.5 g) in dry DMF (25 mL) under argon. NaH (60% in oil, 0.968 g, 24.2 mmol) was added in portions and the mixture was stirred at 50 C for 1 h. The mixture was cooled to rt and bromomethylcyclopropane (3.252 g, 24.2 mmol) was added followed by stirring at rt for 20 h under argon. The reaction mixture was quenched with water and the product extracted into ethyl acetate. The combined organic phases were dried over Na2S04, filtered, and concentrated. The product was purified by flash column chromatography (Si02; n-heptane/ethyl acetate 2: 1) to give the compound 3, 3a- cyclopropylmethoxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (3.354g). 1H NMR (CDCI3) delta 3.98 – 3.94 (m, 2H), 3.44 – 3.40 (m, 1H), 3.05 (d, 2H), 1.96 – 1.88 (m, 2H), 1.79 – 1.62 (m, 6H), 1.29 (s, 9H), 0.88 – 0.79 (m, 1H), 0.35 – 0.30 (m, 2H), 0.04 – 0.00 (m, 2H); 13C NMR (CDCI3) delta 153.4, 78.9, 73.0, 72.5, 52.7, 34.9, 28.5, 28.1, 10.9, 2.8.

Statistics shows that tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate is playing an increasingly important role. we look forward to future research findings about 143557-91-9.

Reference:
Patent; ACADIA PHARMACEUTICALS INC.; BURSTEIN, Ethan, S.; ESKILDSEN, Jorgen; OLSSON, Roger; LUHRS, Lauren, M.; WHEELER, Larry, A.; GIL, Daniel, W.; WO2014/152144; (2014); A1;,
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Electric Literature of 50667-69-1, These common heterocyclic compound, 50667-69-1, name is 2,2,2-Trifluoro-N-(hydroxymethyl)acetamide, 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.

N-(Hydroxymethyl)trifluoracetamide (0.82 g; 5.73 mmol) was added to a mixture of 10 mL conc. H2SO4 and 2-chlor-6-fluorobenzoic acid (1 g; 5.73 mmol) under ice bath cooling and stirred at rt overnight. The mixture was poured into ice, DCM was added, the resulting precipitate was filtered, washed with DCM and water and dried. The residue was purified by HPLC.Yield: 400 mg (23%; Purity: 95%) MS: [M-H]-=298

Statistics shows that 2,2,2-Trifluoro-N-(hydroxymethyl)acetamide is playing an increasingly important role. we look forward to future research findings about 50667-69-1.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/263556; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 20348-09-8, name is 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one, 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 20348-09-8, category: amides-buliding-blocks

To a solution of compound 15 (1 g, 6.66 mmol) in DMF (30 mL) was added dropwise bromine (0.480 mL, 9.32 mmol). The reaction mixture was stirred overnight at room temperature. Water was added and a precipitate was formed which was collected by filtration and dried in lyophilizer overnight to afford title compound 16 (1.16 g, 76% yield). IH NMR (DMSO-d6) delta (ppm): 11.43 (s, IH), 8.04 (d, J = 2.0 Hz, IH), 7.65 (d, J = 2.0 Hz, IH), 4.67 (s,2H).

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, 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; METHYLGENE INC.; WO2009/100536; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics