Amides-buliding-blocks

Reference of 149632-73-5, 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 149632-73-5 as follows.

Under a nitrogen atmosphere, a solution of 3,6-difluoro-9-(oxiran-2-ylmethyl)-9H-carbazole(0.7 g) andtert-butyl (1-aminopropan-2-yl)carbamate(1.5 g) in ethanol (50 mL) was stirred at 70C for 16 hrs. The mixture was concentrated under reduced pressure and purified by silica gel column chromatography, eluting with a gradient of 0-20% methanol in dichloromethane to give an off-white foam (1.28 g). The product was used directly in the next step without additional purification:1H NMR (300 MHz, CDCl3): delta 7.67 (dd, 2H,J= 8.7, 2.7 Hz), 7.42-7.37 (m, 2H), 7.22 (td, 2H,J= 9.0, 2.7 Hz), 4.55-4.30 (m, 3H), 4.13 (m, 1H), 3.78 (br s, 1H), 2.88 and 2.82 (dd, 1H,J= 12.0, 3.6 Hz), 2.70-2.50 (m, 3H), 1.45 (s, 9H), 1.13 and 1.11 (d, 3H,J= 6.6 Hz). ESI (m/z): 434.0 (M+H).

According to the analysis of related databases, 149632-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Humphries, Paul S.; Bersot, Ross; Kincaid, John; Mabery, Eric; McCluskie, Kerryn; Park, Timothy; Renner, Travis; Riegler, Erin; Steinfeld, Tod; Turtle, Eric D.; Wei, Zhi-Liang; Willis, Erik; Bioorganic and Medicinal Chemistry Letters; vol. 28; 3; (2018); p. 293 – 297;,
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Reference of 85006-25-3, 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. 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of tert-butyl (tert-butoxycarbonyl) oxycarbamate (2.71 g, 11.64 mmol) and 1- (bromomethyl) -4-fluorobenzene (2 g, 10.58 mmol) in DCM To the solution was added NaOH (11.64 mL, 11.64 mmol) followed by tetrabutylammonium bromide (3.41 g, 10.58 mmol) and stirred overnight at room temperature. Water (100 mL) was added to the reaction mixture, and the product was extracted with ethyl acetate (3 * 100 mL), and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to give 5.5 g of crude material. The crude material was purified by Iscor using a 40 g silica gel column and the product was eluted with 10% ethyl acetate in petroleum ether to give tert-butyl (tert-butoxycarbonyl) oxy (4-fluorobenzyl) carbamate (3.1 g, 8.99 mmol, 85% yield) as a colorless sticky material.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (tert-butoxycarbonyl)oxycarbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Beu Lease Tol-mai Ground Wire Seukwp Keompeoni; I Seul-ram-, -i-ma-dul; Tang Ga-ti-ru-pa-ti-, -seu-ri-ni-ba-san; Wa Ri-e-reu-, -ja-ya-ku-ma-reu-san-ka-ra; Che Ru-ku-, -seu-ri-ni-ba-seu; Sye Ti-, -pu-reu-ni-ma; Ma Ko-reu-, -jon-i-.; (44 pag.)KR2018/64507; (2018); A;,
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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 2886-65-9 as follows. Computed Properties of C15H10ClFN2O

EXAMPLE 5 8-Chloro-6-(2-fluorophenyl)-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid, ethyl ester Potassium t-butoxide, 1.29 g (0.0115 mol) was added to a stirred solution of 2.88 g (0.01 mol) of 7-chloro-1,3-dihydro-5-(2-fluorophenyl)-2H-1,4-benzodiazepine-2-one in 50 ml of tetrahydrofuran, that had been cooled in an ice bath and covered with a nitrogen atmosphere. After stirring for 5 minutes, 2.59 g (0.015 mol) diethyl chlorophosphate was added. After stirring for 5 minutes, a mixture of 2.26 g (0.02 mol) of ethyl isocyanoacetate in 50 ml of tetrahydrofuran that had been treated with 2.24 g (0.02 mol) of potassium t-butoxide just prior to the addition, was added. After 5 minutes, the ice bath was removed and the stirring was continued for 15 minutes. The mixture was acidified with 2 ml of glacial acetic acid, diluted with 200 ml of saturated sodium bicarbonate solution and extracted twice with 125 ml portions of toluene. The extracts were dried and evaporated and the residue was crystallized from ether to give the product with mp 195-197. For analysis, the material was recrystallized from methylene chloride/ether/hexane to give colorless crystals with mp 195-196. Anal. Calcd for C20 H15 ClFN3 O2: C, 62.59; H, 3.94; N, 10.95. Found: C, 62.59; H, 3.73; N, 11.01.

According to the analysis of related databases, 2886-65-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US4118386; (1978); A;,
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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. 118753-70-1, name is tert-Butyl bis(2-chloroethyl)carbamate, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

B) tert-Butyl 4-cyano-4-(4-fluorophenyl)piperidine-1-carboxylate To a mixture of 33.3 g of 60percent sodium hydride in oil in 200 ml of DMSO and 100 ml of THF is added dropwise, at rt, a solution of 50 ml of 4-fluorophenylacetonitrile and 101 g of the compound obtained in the preceding step in 200 ml of THF, and the mixture is stirred for 2 hours at rt and then refluxed for 1 hour and stirred at rt overnight. The reaction mixture is poured into saturated NH4Cl solution, the THF is concentrated under vacuum, the aqueous phase is diluted with water and extracted with ether, the organic phase is dried over Na2SO4 and the solvent is evaporated off under vacuum. The orange oil obtained is taken up in a minimum amount of ether and the crystalline product formed is filtered off by suction. 87.6 g of the expected product are obtained.

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; SANOFI-AVENTIS; US2007/142349; (2007); A1;,
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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. 138-41-0, name is Carzenide, A new synthetic method of this compound is introduced below., Recommanded Product: 138-41-0

General procedure: To a solution of the carboxylic acids 33-36 (0.45 mmol) indimethylformamide (3 mL), an excess of EDCI (0.54 mmol) andhydroxybenzotriazole monohydrate (0.54 mmol), and a catalytic amount ofdimethylaminopyridine (0.02 mmol) were added. The mixture was stirred at roomtemperature for 2 h, then 5-(4-(aminomethyl)piperidin-1-yl)-2-(furan-2-yl)thiazolo[5,4-d]pyrimidin-7-amine(32) (0.49 mmol) was added. After stirring at room temperature for 3 h,20 mL of H2O were added to precipitate a solid which was filtered,washed with water and purified by column chromatography. N-((1-(7-Amino-2-(furan-2-yl)thiazolo[5,4-d]pyrimidin-5-yl)piperidin-4-yl)methyl)-4-sulfamoylbenzamide(8) Yield 85%. Mp: 166-168 C (column chromatography, eluting system ethylacetate/cyclohexane/methanol 7/2/1). 1H NMR (DMSO-d6): delta 8.71(t, 1H, NHCO, J=5.3 Hz), 8.00(d, 2H, J=8.4 Hz), 7.93-7.83(m, 3H), 7.48 (s, 2H, NH2), 7.24 (s, 2H, NH2), 7.05 (d,1H, J=3.2 Hz), 6.73-6.72 (m,1H), 4.68 (d, 2H, J=12.7 Hz),3.21-3.18 (m, 2H), 2.83 (t, 2H, J=12.0Hz), 1.86 (br s, 1H), 1.75 (d, 2H, J=11.8Hz), 1.14-1.11 (m, 2H). 13C NMR (DMSO-d6): delta 165.82,165.14, 159.21, 157.23, 148.62, 146.61, 145.80, 138.01, 128.34, 126.06, 124.69,113.20, 110.08, 45.35, 44.18, 36.55, 30.08. Anal. calcd. for (C22H23N7O4S2):C, 51.45%; H, 4.51%; N, 19.09%. Anal. found: C, 51.76%; H, 4.85%; N, 19.33%.

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:
Article; Catarzi, Daniela; Colotta, Vittoria; Espindola Gelsleichter, Nicolly; Guilbaud, Audrey; Lopes Rangel Fietto, Juliana; Pasquini, Silvia; Pelletier, Julie; Sevigny, Jean; Sarlandie, Marine; Varani, Katia; Varano, Flavia; Vincenzi, Fabrizio; Bioorganic and medicinal chemistry letters; (2020);,
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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. 84713-20-2, name is Benzyl vinylcarbamate, A new synthetic method of this compound is introduced below., Computed Properties of C10H11NO2

Aniline (3.64 mL, 39.97 mmol, 1.0 equ) was dissolved in methylene chloride (100 mL) and Na2S04 (2 g) was added and cooled to-25 C. Acetaldehyde (2.23 mL, 39.97 mmol, 1.0 equ.) was added to the solution and stirred for Ih at-25 C. Sodium sulfate was filtered off and N-vinyl- carbamic acid benzyl ester (7.07g, 39.97 mmol, 1.0 equiv) was added to the filtrate at-25C, followed by boron triflouride diethyl etherate (0.50 mL, 3.9 mmol, 0.1 equ). The reaction was allowed to stir at -25C for Ih and then warmed to room temperature and stirred for lOh. The reaction was evaporated in vacuo and the residue was purified by Biotage flash system (20% ethyl acetate/80% hexane) to yield 4.0 g, 33 % of (No.)-cis-(2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl)-carbamic acid benzyl ester as a white solid. H’ NMR (300 MHz, CDC13) &:7.38 (m, 5H), 7.17 (d, 1H), 7.02 (t, IH, C7-H), 6.68 (t, IH), 6.47 (d, IH), 5.17 (bs, 2H), 5.07 (m, IH), 4.92 (d, 1H), 3.57 (m, IH), 2.30 (m, IH), 1.47 (q, IH), 1.21 (d, 3H).

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; MILLENNIUM PHARMACEUTICALS, INC.; WO2005/100321; (2005); A1;,
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Reference of 108-13-4,Some common heterocyclic compound, 108-13-4, name is Malonamide, molecular formula is C3H6N2O2, 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.

Step A:; To a solution of anyhydrous methanol (50 mL), sodium methoxide/methanol solution (61.47 mmol) and malonamide (4.50 g, 44.08 mmol) was added (E)-4-ethoxy-l,l,l-trifluoro-3-butene-2-one V-I (7.781 g, 46.28 mmol) and the mixture was heated to reflux for 2 hours. When the reaction was quenched by addition of water and the aqueous layer pH was adjusted to pH 1-3 with HCl. The mixture was concentrated to give compund V-2 (m/z (ES) (M+H)+= 207), which was used in the next step without further purification.

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

Reference:
Patent; MERCK & CO., INC.; WO2007/41052; (2007); A2;,
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Synthetic Route of 96-30-0,Some common heterocyclic compound, 96-30-0, name is 2-Chloro-N-methylacetamide, molecular formula is C3H6ClNO, 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.

The preparation mother liquid (129 mL) of O,O-dimethyl-S-(N-methylcarbamoylmethyl)phosphorothioate in Example 1 which had been reused 6 times was added with methanol to 130 ml. Add 32.82 g (0.2 mol) of the sodium O,O-dimethylthiophosphate prepared in the step (2), 21.5 g (0.2 mol) of 2-chloro-N-methylacetamide prepared in the step (1) and 1.66 g (0.01 mol) of potassium iodide were reacted at 65 C for 10 hours, and then the heating was stopped. After naturally dropping to room temperature, the salt formed by the reaction is filtered off, Rotating to remove the solvent, That is, 40.98 g of light yellow O,O-dimethyl-S-(N-methylcarbamoylmethyl)phosphorothioate was obtained, the yield was 96.1%; The purity by GC was 95.22%; the water content of the product was 0.044%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-N-methylacetamide, its application will become more common.

Reference:
Patent; Henan Chemical Institute Co., Ltd.; Huo Erfu; Cheng Weiqin; Feng Ming; Wang Bonan; Wang Yanhua; Chang Shuhao; Dong Guangxia; Yang Shuai; Wang Yinan; (16 pag.)CN109651432; (2019); A;,
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Related Products of 24036-52-0, A common heterocyclic compound, 24036-52-0, name is 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, molecular formula is C8H6BrNO2, 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: To a solution of 5 (350mg, 1.54mmol) in 20mL THF was added phenylboronic acid (3.28mmol), copper acetate (420mg, 2.31mmol), Et3N (0.5mL, 4.62mmol) and 4A molecular sieve (50mg). The solution was stirred at 60C for 6h. After the completion of the reaction (monitored by TLC), the reaction solution was concentrated, and added with 20mL water. The reaction was filtered to remove solids and extracted with EtOAc, the organic layer was collected and washed with saturated salt solution for three times, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude material was purified by column chromatography to afford target product.

The synthetic route of 24036-52-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yan, Guoyi; Pu, Chunlan; Lan, Suke; Zhong, Xinxin; Zhou, Meng; Hou, Xueyan; Yang, Jie; Shan, Huifang; Zhao, Lifeng; Li, Rui; European Journal of Medicinal Chemistry; vol. 178; (2019); p. 667 – 686;,
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Reference of 6331-71-1, 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. 6331-71-1, name is 4-Amino-N,N-dimethylbenzamide, This compound has unique chemical properties. The synthetic route is as follows.

[00258] Compound 38 [00259] [00261] [00262] To a mixture of 4-chloro-6-((4,7-difluoro-2-methyl-lH-indol-5- yl)oxy)pyrimidine-5-carbonitrile (80 mg, 0.25 mmol) and 4-amino-N,N-dimethylbenzamide (49 mg, 0.30 mmol) in anhydrous DMSO (1.5 mL) was added TEA (0.122 mL; 0.875 mmol), and the resulting biphasic mixture was efficiently stirred at room temperature for ca. 3 days. The resulting mixture was diluted with EtOAc (100 mL) and washed with aq. NaHC03 (ca. 100 mL each; 50% NaHC03 saturation). The organic layer was separated and dried over anhydrous Na2S04 and concentrated. The resulting residue was purified by crystallization (DCM) to afford the desired product as a white solid (49 mg, 44% yield). 1H NMR (DMSO- d6, 400 MHz) delta 11.85 (br s, 1H), 10.20 (br s, 1H), 8.33 (s, 1H), 7.60 (d, J = 8.4 Hz, 2H), 7.41 (d, J = 8.4 Hz, 2H), 7.04-7.00 (m, 1H), 6.35 (s, 1H), 2.97 (s, 6H), 2.42 (s, 3H); MS (ESI): calcd for C23H18F2N602: 448, found: 449 (MH+).

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

Reference:
Patent; NANTBIOSCIENCE, INC.; TAO, Chunlin; POLAT,, Tulay; WEINGARTEN, Paul; NALLAN, Laxman; ARP, Forrest; WANG, Qinwei; HO, David; (129 pag.)WO2016/138527; (2016); A1;,
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