Tag: M.W=100-200

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. 102562-86-7, name is 3-(Aminomethyl)benzamide, A new synthetic method of this compound is introduced below., Recommanded Product: 3-(Aminomethyl)benzamide

To a solution of Intermediate 1h (50 mg, 0.152 mmol) and 3-aminomethyl-benzamide (60 mg, 0.228 mmol) in 2 mL DMF, were added iPr2Net (106 muL, 0.608 mmol), HOAT (41.4 mg, 0.304 mmol) and EDCI (35 mg, 0.182 mmol). The mixture was stirred at rt for 14 h, then was diluted with EtOAc. The organic phase was washed with H2O, 1N HCl, H2O, 0.1 N, NaOH, and brine, dried (Na2SO4), and concentrated. The crude product was recrystallized from methanol to afford 7.2 mg (10%) of Example 24. MS (HR-ESI) calculated for C24H24N5O5 (M+H+), found 462.1787; MS (ESI) 462.3 (M+H+), 484.3 (M+Na+); 1H NMR (300 MHz, CD3OD) delta. 8.51 (br. S, 1H), 7.84 (s, 1H), 7.78 (d, J=7.7, 1H), 7.53-7.31 (m, 7H), 5.20 (s, 2H), 5.13 (dd, J=3.0, 1.0, 1H), 4.61-4.37 (m, 2H), 3.25-3.16 (m, 1H), 3.12-3.03 (m, 1H), 2.66-2.55 (m, 1H), 2.32-2.24 (m, 1H).

The synthetic route of 102562-86-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glunz, Peter W.; US2004/6065; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 683-57-8, name is 2-Bromoacetamide, 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 683-57-8, category: amides-buliding-blocks

The product of Example 323C (0.025 g, 0.057 mmol) was reacted with cesium carbonate (0.055 g, 0.17 mmol), 2-bromoacetamide (0.012 g, 0.087 mmol) and a catalytic amount of tetrabuylammonium iodide in N,N-dimethylformamide (3 ML) at 25 C. for 2 hours.The reaction was concentrated to half the volume under a stream of nitrogen warmed through a manifold heated to 165 C. The resulting solution was diluted with water and the precipitate was collected by filtration and dried to give the title compound (0.020 g, 72%). MS (ESI-) m/z 498 (M-H)-.The sodium salt of the title compound was prepared according to the procedure of Example 1D. 1H NMR (300 MHz, DMSO-d6) delta ppm 0.90 (m, 3 H) 1.33 (m, 6 H) 1.54 (m, 2 H) 4.49 (s, 2 H) 5.90 (m, 1 H) 7.06 (m, 1 H) 7.21 (m, 2 H) 7.40 (m, 1 H) 7.55 (m, 2 H) 8.07 (dd, J=8.27, 1.29 Hz, 1 H) 16.23 (s, 1 H).

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; Pratt, John K.; Betebenner, David A.; Donner, Pemela L.; Green, Brian E.; Kempf, Dale J.; McDaniel, Keith F.; Maring, Clarence J.; Stoll, Vincent S.; Zhang, Rong; US2004/87577; (2004); A1;,
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25412-53-7, name is 4-Acetamidobenzylamine, belongs to amides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 25412-53-7

EXAMPLE 50 N-(4-acetylamino-phenylmethyl)-3-(4′-trifluoromethylbiphenyl-2-carbonylamino)-benzoic acid amide Prepared analogously to Example 7 from 3-(4′-trifluoromethylbiphenyl-2-carbonylamino)-benzoic acid and 4-acetylaminobenzylamine in dichloromethane with the addition of propanephosphonic acid cycloanhydride and N-methylmorpholine. Yield:38% of theory Rf value:0.60 (silica gel; dichloromethane/ethanol=9:1)

The synthetic route of 25412-53-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Priepke, Henning; Hauel, Norbert; Thomas, Leo; Mark, Michael; Dahmann, Georg; US2002/32238; (2002); A1;,
Amide – Wikipedia,
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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,
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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. 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;,
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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

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 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

Related Products of 25900-61-2, 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 25900-61-2 as follows.

Step 2To 2-chloro-5-fluoro-4-(3-(4-fluorophenoxy)azetidin-l-yl)pyrimidine (90.0 mg, 0.302 mmol) and 3-amino-N-methylbenzamide (49.9 mg, 0.333 mmol) in a disposable sealed tube in 2-propanol (2.50 mL) was added trifluoroacetic acid (0.070 mL, 0.907 mmol). The resulting reaction mixture was heated at 84 C for 3 d, cooled to RT and concentrated. The residue was stirred in EtOAc and saturated aqueous NaHC03 for 10 min and transferred to a separatory funnel. The organic layer was washed with brine, dried and concentrated giving 3-(5-fluoro-4- (3 -(4-fluorophenoxy)azetidin- 1 -yl)pyrimidin-2-ylamino)-N-methylbenzamide ( 124.8 mg).

According to the analysis of related databases, 25900-61-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John, L.; CHAKKA, Nagasree; DIMAURO, Erin, F.; DU, Bingfan; NGUYEN, Hanh, Nho; ZHENG, Xiao, Mei; WO2011/103196; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 402-46-0, A common heterocyclic compound, 402-46-0, name is 4-Fluorobenzenesulfonamide, molecular formula is C6H6FNO2S, 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: The synthesis route of compounds 1-24 followed the general pathway outlined in Scheme 1. The substituted nicotinic acid (1 mmol) mixed with benzenesulfonamide (1 mmol) through by using 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl) (1.2 mmol) and 4-dimethylaminopyridine (DMAP) (1.2 mmol) in anhydrous CH2Cl2 for 6-8 h at 70-80 C. The reaction was monitored by TLC. The products are extracted with ethyl acetate. The extract is washed successively with 1 N HCl, water, 1 M NaHCO3, and water, dried over MgSO4, filtered and evaporated. The residue is purified by column chromatography using petroleum ether and ethyl acetate (1:1).

The synthetic route of 402-46-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Hui; Lu, Xiang; Zhang, Li-Rong; Liu, Jia-Jia; Yang, Xian-Hui; Wang, Xiao-Ming; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 20; 4; (2012); p. 1411 – 1416;,
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