Month: August 2021

Synthetic Route of 86499-35-6, These common heterocyclic compound, 86499-35-6, name is 3-Amino-2,3,4,5-tetrahydro-1H-benzazepin-2-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.

Example 6-4 Synthesis of 3-(N’-(3,5-Difluorophenylacetyl)-L-alaninyl)amino-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one Following General Procedure A above using N-(3,5-difluorophenylacetyl)-L-alanine (Example B) and 3-amino-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (General Procedure 6-B), the title compound was prepared. The reaction was monitored by tlc on silica gel (Rf=0.15 in 12% methanol/dichloromethane) and purification was by flash chromatography using 12% methanol/dichloromethane as the eluant. NMR data was as follows: 1H-nmr (CDCl3): delta=9.87 (s, 1H), 8.28 (d, 1H), 8.11 (d, 1H), 7.30-6.96 (m, 7H), 4.23 (m, 1H), 4.18 (m, 1H), 3.49 (s, 2H), 2.68 (m, 2H), 2.24 (m, 1H), 1.97 (m, 1H), 1.15 (s, 3H). 13C-nmr (CDCl3): delta=171.95, 171.54, 189.00, 160.74, 141.06, 138.01, 133.91, 129.90, 127.84, 125.58, 122.41, 112.79, 112.46, 102.23, 49.06, 48.47, 41.67, 35.50, 28.39, 18.99.

Statistics shows that 3-Amino-2,3,4,5-tetrahydro-1H-benzazepin-2-one is playing an increasingly important role. we look forward to future research findings about 86499-35-6.

Reference:
Patent; Wu, Jing; Tung, Jay S.; Thorsett, Eugene D.; Pleiss, Michael A.; Nissen, Jeffrey S.; Neitz, Jeffrey; Latimer, Lee H.; John, Varghese; Freedman, Stephen; Britton, Thomas C.; Audia, James A.; Reel, Jon K.; Mabry, Thomas E.; Dressman, Bruce A.; Cwi, Cynthia L.; Droste, James J.; Henry, Steven S.; McDaniel, Stacey L.; Scott, William Leonard; Stucky, Russell D.; Porter, Warren J.; US2002/45747; (2002); 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. 191170-76-0, name is Benzyl 4-bromophenethylcarbamate, A new synthetic method of this compound is introduced below., SDS of cas: 191170-76-0

(1402) [00449] To a vial was added benzyl 4-bromophenethylcarbamate (0.337 g, 1.01 mrnol), tert- butyl 3,6-diazabicyclo[3.1.1]heptane-3-carboxylate (0.200 g, 1.01 mmoi), CS2CO3 (0.822 g, 2.52 mmoi), and XPhos Pd 2nd generation precatalyst (0.079 g. 0.10 mmoi). The vial was backfilled with dry nitrogen 3 times. Dioxane (2 ml) was added to the solid mixture and a stream of dry nitrogen was bubbled through the reaction for 2 minutes. The reaction mixture was heated to 90 C overnight and then cooled to RT, filtered through Celite and concentrated in vacuo. The resulting crude product was purified by FCC eluting with 20 – 30% EtOAc in hexanes to afford teri-mXy 6-(4-(2-(((benzyloxy)carbonyl)amino)ethyl)phenyl)-3,6-diazabicyclo[3.1 .1 ]heptane~3- carboxylate as a white solid (322 mg, 71%). LCMS (ESI, m/z): 452 [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; FORMA THERAPEUTICS, INC.; GUERIN, David Joseph; BAIR, Kenneth W.; CARAVELLA, Justin A.; IOANNIDIS, Stephanos; LANCIA JR., David R.; LI, Hongbin; MISCHKE, Steven; NG, Pui Yee; RICHARD, David; SCHILLER, Shawn E. R.; SHELEKHIN, Tatiana; WANG, Zhongguo; (365 pag.)WO2017/139778; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 25900-61-2, name is 3-Amino-N-methylbenzamide, molecular formula is C8H10N2O, 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. Recommanded Product: 3-Amino-N-methylbenzamide

General procedure: To a solution of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-1H-indazole-4-carboxylic acid (8, 30 mg,0.082 mmol) in pyridine (3 mL) at 0 C. POCl3 (12 L, 0.090 mmol) was added, and the mixture wasstirred at 0 C for 1 h. Aniline was added into the reaction mixture and stirred at 0 C for 10 min, then,the mixture was stirred at 25 C for 1.5 h. The reaction was quenched with distilled water, and theorganic phase was washed with water, 1N HCl and brine, dried over Na2SO4, filtered and concentratedin vacuo. The resultant residue was purified by column chromatography to get the final product as awhite solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 25900-61-2, its application will become more common.

Reference:
Article; Zhang, Zhen; Zhao, Dongmei; Dai, Yang; Cheng, Maosheng; Geng, Meiyu; Shen, Jingkang; Ma, Yuchi; Ai, Jing; Xiong, Bing; Molecules; vol. 21; 10; (2016);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 101-21-3, 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. 101-21-3, name is Isopropyl (3-chlorophenyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A coprecipitation method was carried out to prepare the complex. beta-CD (2.270 g, 2.0 mmol) and CIPC (0.214 g, 1.0 mmol) were ground into powder together, then were completely dissolved in 100 mL of solution of ethanol and water (v/v = 1:5). The solution was stirred at 70C for 24 h, then ethanol was evaporated and the reaction mixture was cooled at 4C overnight. The precipitate was filtered and washed by a little doubly distilled water and ethanol,respectively. The obtained solid was dried to constant weight in a vacuum desiccator.

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, Isopropyl (3-chlorophenyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ge, Xia; He, Jiang; Qi, Fengming; Yang, Ying; Huang, Zheng; Lu, Ruihua; Huang, Lizhen; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 81; 1; (2011); p. 397 – 403;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 89979-12-4, name is 5-Chloro-2-(methylsulfonamido)benzoic acid, 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 89979-12-4, Formula: C8H8ClNO4S

Mixed 5-chloro-2-(methylsulfonamido)benzoic acid (47mg, 0.187mmol) with HATU (71mg, 0.187mmol) and dissolved in anhydrous DMF (lmL). Stirred for lhr. Dissolved amine hydrogen chloride (49mg, 0.17mmol) in anhydrous DMF (lmL) and added to the reaction. Added TEA (71uL, 0.5 lmmol). Stirred for 16 hrs. Diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution twice. Dried organic extract over anhydrous sodium sulfate and then concentrated under reduced pressure. Purified with silica gel column (0-50% EtOAc in hexanes) to give intermediate 55 (57mg, 39% yield). LC/MS (m/z): 482.2 [M+H]+

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, 5-Chloro-2-(methylsulfonamido)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GILEAD SCIENCES, INC.; BABAOGLU, Kerim; BOOJAMRA, Constantine, G.; EISENBERG, Eugene, J.; HUI, Hon Chung; MACKMAN, Richard, L.; PARRISH, Jay, P.; SANGI, Michael; SAUNDERS, Oliver, L.; SIEGEL, Dustin; SPERANDIO, David; YANG, Hai; WO2011/163518; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 141449-85-6, name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, 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 141449-85-6, Product Details of 141449-85-6

A solution of (4-Chloro-5-methyl-3-trifluoromethylpyrazol-1-yl) acetic acid (97 mg), triethylamine (0.2 mL) and compound 5 (76 mg) in DMF (2 mL) was stirred at 0 C and 1-propanephosphonic acid cyclic anhydride (0.55 mL, 50% in EtOAc) was added dropwise. The reaction mixture was stirred another 30 min at 0 C and directly purified by preparative HPLC to provide the title compound 6 as a pale yellow oild (146 mg, 93%). LCMS: Rf: 4.495 min, M+H+ : 459.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2005/84667; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 5004-88-6, 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. 5004-88-6, name is 2-Amino-4,5-dimethoxybenzamide, This compound has unique chemical properties. The synthetic route is as follows.

[0281] To a mixture of 2-amino-4,5-dimethoxybenzamide (8.42g, 38.86 mmole) and pyridine (11.64g, 147.4 mmole) in CHCl3 (180 mL) was added 3-phenylbenzoyl chloride (7.23g, 36.86 mmole) and the reaction was stirred at RT for 5 h. The volatiles were removed in vacuo and the product 2-(benzoylamino)-4,5-dimethoxybenzamide was used immediately without future purification. HPLC retention time 7.92 mins.

The chemical industry reduces the impact on the environment during synthesis 2-Amino-4,5-dimethoxybenzamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SURFACE LOGIX, INC.; BARTOLOZZI, Alessandra; SWEETNAM, Paul; WO2006/105081; (2006); A2;,
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. 915087-25-1, name is 4-Amino-2-fluoro-N-methylbenzamide, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Amino-2-fluoro-N-methylbenzamide

Example 44 4-({2-[4-(2-Cyano-5-methylphenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(1-methyl-1H-pyrazol-3-yl)propanoyl}amino)-2-fluoro-N-methylbenzamide (Racemate) 50 mg (0.09 mmol, 80% purity) of 2-[4-(2-cyano-5-methylphenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(1-methyl-1H-pyrazol-3-yl)propanoic acid hydrochloride (racemate) and 24 mg (0.14 mmol, 1.5 eq.) of 4-amino-2-fluoro-N-methylbenzamide were initially charged in 0.8 ml of pyridine, 89 mul (0.37 mmol, 50% in ethyl acetate, 4.0 eq.) of T3P were added and the mixture was stirred at 50 C. for 2 h. The reaction mixture was cooled and purified by means of preparative HPLC (RP18 column, eluent: acetonitrile/water gradient with addition of 0.1% formic acid). Yield: 40 mg (79% of theory). LC/MS [Method 1]: Rt=0.82 min; MS (ESIpos): m/z=543 (M+H)+, 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=10.87 (s, 1H), 8.12-8.03 (m, 1H), 7.80 (d, 1H), 7.71-7.61 (m, 2H), 7.54 (s, 1H), 7.52 (d, 1H), 7.45-7.39 (m, 2H), 7.36 (s, 1H), 6.35 (s, 1H), 5.99 (d, 1H), 5.87 (dd, 1H), 3.74 (s, 3H), 3.65 (s, 3H), 3.54-3.39 (m, 2H), 2.77 (d, 3H), 2.41 (s, 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; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHRIG, Susanne; JIMENEZ NUNEZ, Eloisa; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; TELLER, Henrik; HILLISCH, Alexander; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; STAMPFUss, Jan; (82 pag.)US2017/298052; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 518057-72-2, name is 5-Amino-2-fluorobenzamide, 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 518057-72-2, Computed Properties of C7H7FN2O

Racemic fr 5-4-[2-Methoxy-4-(trifluoromethoxy)phenoxy]-6-(2- methylcyclopropyl)pyridine-3-carboxylic acid (103 mg, 0.269 mmol) and HATU (103 mg, 0.271 mmol) were combined in DMF (1 mL) and DIEA (94 mu, 0.54 mmol) and stirred for 5 minutes. 5-Amino-2- fluoro-benzamide (62 mg, 0.40 mmol) was added in one portion and the reaction stirred at 45 C for 1 hour. The reaction was diluted with ethyl acetate and washed with 50% saturated aqueous NaHCC and brine, dried over Na2S04, filtered, and concentrated in vacuo. Silica gel chromatography (0-15% methanol/dichloromethane) provided racemic fras-N-(3-carbamoyl-4-fluoro-phenyl)-4-[2-methoxy-4- (trifluoromethoxy)phenoxy]-6-(2-methylcyclopropyl)pyridine-3-carboxamide (135 mg, 95%). ESI-MS m/z calc. 519.14, found 520.2 (M+l)+; retention time (Method B): 1.36 minutes (3 minute run). ‘H NMR(400 MHz, DMSO-d6) delta 10.38 (s, 1H), 8.54 (s, 1H), 7.99 (dd, J = 6.4, 2.8 Hz, 1H), 7.82 (ddd, J = 8.9, 4.4, 2.8 Hz, 1H), 7.70 (s, 1H), 7.67 (s, 1H), 7.45 (d, J = 8.8 Hz, 1H), 7.32 – 7.21 (m, 2H), 7.07 (ddd, J = 8.8, 2.7, 1.3 Hz, 1H), 6.55 (s, 1H), 3.80 (s, 3H), 1.81 (dt, J = 8.5, 4.4 Hz, 1H), 1.38 – 1.25 (m, 1H), 1.16 – 1.11 (m, 1H), 1.10 (d, J = 6.0 Hz, 3H), 0.74 (ddd, J = 9.0, 5.9, 3.6 Hz, 1H) ppm. SFC purification (36% methanol/64% CO2, ChiralPak IG (250 x 21.2 mm) 5muiotaeta column, flow =70 mL/min) provided separated enantiomers re/-N-(3-carbamoyl-4-fluoro-phenyl)-4-[2-methoxy-4-(trifluoromethoxy)phenoxy]-6- ((lS,2S)-2-methylcyclopropyl)pyridine-3-carboxamide (113) and re/-N-(3-carbamoyl-4-fluoro-phenyl)-4- [2-methoxy-4-(trifluoromethoxy)phenoxy]-6-((lR,2R)-2-methylcyclopropyl)pyridine-3-carboxamide (114). The absolute stereochemistry of enantiomers 113 and 114 was not determined.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Amino-2-fluorobenzamide, and friends who are interested can also refer to it.

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;,
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 147291-66-5 as follows. Computed Properties of C12H18N2O2

The oil was dissolved in 100 ml of THF, and 3.66 ml of DIPEA and then dropwise 2.60 g of benzyl isocyanate were added to the solution. The mixture was stirred at RT for 16 h, then under reflux for 6 h and then at RT for a further 16 h. It was concentrated and crystallized from 30 ml of ethyl acetate, and the resulting precipitate was filtered off with suction and dried; 4.90 g; ESI-MS [carbamic acid fragment+H+]=300.

According to the analysis of related databases, 147291-66-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Abbott GmbH & Co. KG; US7105508; (2006); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics