Category: amides-buliding-blocks

Electric Literature of 389890-42-0, 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. 389890-42-0, name is tert-Butyl (trans-3-hydroxycyclobutyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 26-b To a solution of intermediate 8-b (2.0 g, 10.7 mmol) in anhydrous THF (53 ml) cooled to 0C was slowly added a 1.0 M solution of LiAIH4 in THF (32.0 ml, 31.0 mmol). After the addition was completed, the reaction was warmed to room temperature, stirred at 65C for 2 hours and then cooled to 0C. 15% aqueous NaOH was then added and after stirring for 15 minutes the reaction was filtered. The filtrate was concentrated under reduced pressure. Purification by silica gel chromatography provided intermediate 26-b as a white solid.

The synthetic route of tert-Butyl (trans-3-hydroxycyclobutyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMASCIENCE INC.; LAURENT, Alain; ROSE, Yannick; MORRIS, Stephen J.; (184 pag.)WO2016/187723; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 3984-14-3 as follows. HPLC of Formula: C2H8N2O2S

2-(1H-indoi-6-yl)-3-[4-(tetrahvdro-pyran-4-yioxymethyi)-phenyiethynvi-benzoic acid (45.1 rng, 0.1 mrnol) and dimethylsulfarnoyl amine (149 mg, 0.14 rnrnoi) were dissolved in N,Ndimethyiforinarnide (1 mL), followed by the addition of 1-ethyl-3-(3-dimethyiaminopropyl)carbodiimide hydrochloride (1.2 eq), 4-dimethylarninopyii dine (2 eq) and hydroxybenzotriazole (1.2 eq). The reaction was stirred at room temperature for 16 hours. The solvent was then evaporated to dryness and reaction mixture was purified by preparative HPLC to give product as an off-white solid in 68% yield. ?H NMR (300 MHz, CDCI3) d ppm 8.39 (hr. s., I H) 7.71-7.86 (in, 3 Fl) 7.54 (s, I H) 7.39-7.51 (m, 2 H) 7.20-733 (m, 4 H) 716 (d, .J=7.92 Hz, 2 H) 7.01 (d, J=8.21 Hz, 2 H) 6.63 (br. s.,1 H) 4.49 (s, 2 H) 3.88-4.06 (m, 2 H) 3.37-3.61 (in, 3 H) 2.56 (s, 6 H) 1.82-1.99 (m, 2 H) 1.54-1.75 (in. 2 H,). MS m/z (M-i-H) 558.2.

According to the analysis of related databases, 3984-14-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE WISTAR INSTITUTE OF ANATOMY AND BIOLOGY; MESSICK, Troy E.; SMITH, Garry R.; REITZ, Allen B.; LIEBERMAN, Paul M.; MCDONNELL, Mark E.; ZHANG, Yan; CARLSEN, Marianne; CHEN, Shuai; (205 pag.)WO2016/183534; (2016); A1;,
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Amide – an overview | ScienceDirect Topics

Reference of 6971-74-0, These common heterocyclic compound, 6971-74-0, name is N-Tosylbenzamide, 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: N-Benzoylsulfonamide 1a (27.5 mg, 0.1 mmol), [RhCl2Cp*]2 (1.2 mg, 0.002 mmol), and Cu(OAc)2¡¤H2O (40.0 mg, 0.20 mmol) were loaded in a dry vial, which was subjected to evacuation/flushing with dry argon three times. An anhydrous toluene (1.0 mL) solution of ethyl diazoacetate 4a (30 muL, 0.30 mmol) was syringed into the mixture, which was then stirred at 130 C for 24 h or until the starting material had been consumed as determined by TLC. Upon cooling to room temperature, all volatiles were evaporated and the residue was purified by preparative TLC (ethyl acetate/hexane=1:2) to give isoindolinone 3i in 80% yield.

The synthetic route of 6971-74-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhu, Chen; Falck, John R.; Tetrahedron; vol. 68; 45; (2012); p. 9192 – 9199;,
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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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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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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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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;,
Amide – Wikipedia,
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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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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

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