Amides-buliding-blocks

Electric Literature of 24167-52-0,Some common heterocyclic compound, 24167-52-0, name is 3-Chloro-N,N-dimethylbenzamide, molecular formula is C9H10ClNO, 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’-cyanobenzimidamide (16.8 g, 115 mmol)And Compound 1-2 (21 g, 115 mmol) and phosphorous oxychloride (12 mL, 128 mmol) was dissolved in 500 mL of acetonitrileAnd the mixture was refluxed with stirring for 1 hour.After cooling to room temperature, the resulting solid was filtered,Washed with water and ethanol, and dried to give Compound 1-3. (27.6 g, 80% yield)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-N,N-dimethylbenzamide, its application will become more common.

Reference:
Patent; LG Chem, Ltd.; Cho Seong-mi; Lee Jeong-ha; Lee Dong-hun; Park Tae-yun; Moon Jeong-uk; Jeong Min-u; (39 pag.)KR2018/55688; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 96-30-0, name is 2-Chloro-N-methylacetamide, 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 96-30-0, Quality Control of 2-Chloro-N-methylacetamide

4-(BOC-amino)pirhoeridine hydrochloride (1.06 g) was partitioned between DCM (75 ml) and saturated aqueous Na2CO3 solution (75 ml). The aqueous layer was separated and extracted with DCM (50 ml). The organic layers were combined, dried over MgSO4, filtered and concentrated in vacuo. The resulting white powder was dissolved in dry DMF (20 ml) under nitrogen and to this mixture was added Na2CO3 (617 mg) and 2- chloro-JV-methylacetamide (626 mg). The reaction mixture was stirred at room temperature for 24 hours. Water (80 ml) was added and the mixture was extracted with DCM (2 x 100 ml). The organic layers were combined, dried over MgSO4, filtered and concentrated in vacuo. The residue was suspended in dry MeOH (10 ml) under nitrogen and to it was slowly added 2N HCl in Et2O (10 ml). The mixture was stirred at room temperature for 5 hours. The solvent was removed in vacuo and the residue was triturated in Et2O to afford the title compound as a white solid (1.2 g, 94%). LCMS 172 [M+H]+ (free base), RT 0.29 min. 1H NMR 300 MHz (d6-DMSO) 10.30-10.10 (1H, m, br), 8.80- 8.30 (4H, m, br), 4.00-3.70 (3H, m, br), 3.60-3.00 (4H, m), 2.55 (3H3 s, br), 2.20-1.80 (4H, m).

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, 2-Chloro-N-methylacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CELLTECH R & D LIMITED; WO2006/38001; (2006); 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 177906-48-8 as follows. SDS of cas: 177906-48-8

To a stirred mixture of 6-chloroquinoline-2-carboxylic acid (100 mg, 0.48 mmol, 1 equiv) and trans-tert-butyl (4-aminocyclohexyl)carbamate (103 mg, 0.48 mmol, 1 equiv) in DMF (5 mL) was added HATU (365 mg, 0.96 mmol, 2 equiv) and continued stir at RT for 30 min. DIPEA (0.3 ml, 1.44 mmol, 3 equiv) was added and again stirred at RT for overnight. Reaction progress was monitored by LCMS. After completion of reaction, the reaction mixture was poured into water (50 mL), the resulting yellow precipitate was filtered off and again washed with water (20 mL×2). Thus obtained solid was dried under vacuum to obtain trans-tert-butyl (4-(6-chloroquinoline-2-carboxamido)cyclohexyl)carbamate (120 mg, 71.85%) as a yellow solid. LCMS: 404.6 [M+H]+

According to the analysis of related databases, 177906-48-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Praxis Biotech LLC; BERNALES, Sebastian; DELGADO OYARZO, Luz Marina; NUNEZ VASQUEZ, Gonzalo Esteban; URETA DIAZ, Gonzalo Andres; PUJALA, Brahmam; PANPATIL, Dayanand; BHATT, Bhawana; CHAKRAVARTY, Sarvajit; US2019/177310; (2019); A1;,
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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. 610302-03-9, name is tert-Butyl (3-hydroxycyclohexyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C11H21NO3

Step 1. tert-Butyl (3-((4- bromobenzyl)oxy)cyclohexyl)carbamate. To a stirring solution of tert-butyl (3- hydroxycyclohexyl)carbamate (220 mg, 1.02 mmol) in THF (3 mL) at 0 C was added NaH (41 mg, 1.02 mmol) and stirred at 0 C for 30 mins, then 4-bromobenzyl bromide (255 mg, 1.02 mmol) was added and the reaction mixture was warmed to rt and stirred for 3h. The reaction mixture was cooled to 0 C, and quenched by the dropwise addition of sat. ammonium chloride, extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography using 10 – 25% EtOAc/Hexanes gradient elution to afford tert-butyl (3-((4- bromobenzyl)oxy)cyclohexyl)carbamate as a white solid (184 mg, 48%): NMR (500MHz, CDCk) delta ppm 7.45 (d, J= 8.3 Hz, 2H), 7.21 (d, J= 2H), 4.92 (bs, 1H), 4.48 (s, 2H), 3.55 (m, 1H), 3.45 (bs, 1H), 2.19 (d, 11.72 Hz, 1H), 1.70 – 1.95 (m, 3H)1.44 (s, 9H), 1.15 – 1.37 (m, 4H).

The synthetic route of 610302-03-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHEASTERN UNIVERSITY; MALAMAS, Michael; MAKRIYANNIS, Alexandros; SUBRAMANIAN, Kumara Vadivel; WHITTEN, Kyle M.; ZVONOK, Nikolai M.; WEST, Jay Matthew; MCCORMACK, Michael; PAVLOPOULOS, Spiro; WO2015/179190; (2015); A1;,
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1103234-56-5, name is 2,6-Difluoro-3-(propylsulfonamido)benzoic acid, 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. Recommanded Product: 2,6-Difluoro-3-(propylsulfonamido)benzoic acid

Example 4Propane-1 -sulfonic acid {3-[5-(4-chloro-phenyl)-1 H-pyrrolo[2,3-b]pyridine-3-carbonyl]- 2,4-difluoro-phenyl}-amide (1 )A suspension of sulfonamide acid (9) (1 .2 eq.) in CH2CI2 was treated at roomtemperature with cat. amount of DMF (0.1 1 eq.). Within 30 min a solution ofoxalylchloride (1 .30 eq.) in CH2CI2 was added and the reaction mixture was stirred for 2 h, whereby the corresponding acid chloride was formed. A suspension of aluminium chloride (AICI3, 4 eq.) in CH2CI2 was treated at 0C with a solution of Cl-phenyl azaindole (8) in CH2CI2. To the reaction mixture was subsequently added at room temperature the freshly prepared (above described) acid chloride. Stirring at room temperature for 3 h, aqueous work-up and crystallization from THF/heptane provided the title compound (1 ) as off-white powder in 85% yield. MS (Turbo Spry): 509 (48%), 507 (M+NH4+, 100%), 492 (40%), 490 (M+H+, 84%).

The synthetic route of 1103234-56-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BRUMSTED, Corey James; MOORLAG, Hendrik; RADINOV, Roumen Nikolaev; REN, Yi; WALDMEIER, Pius; WO2012/10538; (2012); A2;,
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Application of 40724-47-8, These common heterocyclic compound, 40724-47-8, name is 4-Bromomethylbenzenesulfonamide, 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.

In this example, Compound 1 of the Scheme 2 is coupled with compound 2 of Scheme 2 at the presence of an activating agent BOP to give product 3 of Scheme 2, which then alkylated with substituted benzyl bromide 4 of Scheme 2 to produce the desired product 6 of Scheme 2 and by product 5 of Scheme 2. Compound 6 of Scheme 2 is purified by a silica gel column and then reacted with TFA to cleave the Boc group. Compound 7 of Scheme 2 is alkylated with benzyl bromide, and the reaction mixture is purified by HPLC to yield final product compound of Formula I, which in the exemplified scheme is a white solid with purity >98percent, overall yield about 32percent.

Statistics shows that 4-Bromomethylbenzenesulfonamide is playing an increasingly important role. we look forward to future research findings about 40724-47-8.

Reference:
Patent; INTRA-CELLULAR THERAPIES, INC.; LI, Peng; PENG, Youyi; TOMESCH, John; WENNOGLE, Lawrence P.; ZHANG, Qiang; (15 pag.)US2018/333403; (2018); A1;,
Amide – Wikipedia,
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These common heterocyclic compound, 6274-22-2, name is 4-Amino-N-methylbenzamide, 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. Formula: C8H10N2O

Example 27; 4-({4-[(1 ,1 -Dimethylethyl)amino]-1 W-pyrrolo[2,3-d]pyrimidin-2-yl}amino)-lambda/-met hylbenzamide trifluoroacetate; lambda/-(1 J-dimethylethyl)-2-iodo-7-[(4-methylphenyl)sulfonyl]-7/-/-pyrrolo[2,3-c(]pyrimidin- 4-amine (O.betammol) was dissolved in DMF (16ml). Bis(dibenzylideneacetone) palladium (10mol%, Aldrich), 2-dicyclohexylphosphino-2′-(lambda/,lambda/-dimethylamino) biphenyl (15mol%), cesium carbonate (0.3mmol) and 4-amino-lambda/-methylbenzamide (0.15mmol) were combined with an aliquot of this solution (2ml). The reaction was heated at 800C for 2h, allowed to cool, filtered through Celite and concentrated. The reaction was dissolved in methanol (1.5ml), treated with sodium methoxide in methanol (0.5M, 500mul), stirred at 700C for 2h and left to stand at room temperature overnight. The reaction was heated for a further 5h, concentrated and purified using MDAP. The fractions containing product were evaporated to dryness to give title compound (3mg). LC/MS; Rt 2.58min, MH+ 339.

The synthetic route of 4-Amino-N-methylbenzamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/42298; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 98-18-0, name is 3-Aminobenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 98-18-0

A solution of 3-aminobenzenesulfonamide (271.9 mg, 1.58 mmol), 4,5- dichloro-2-fluoro-benzoic acid (300 mg, 1.43 mmol), and HATU (654.8 mg, 1.72 mmol) in DMF (3.12 mL) was treated with N-methylmorpholine (315.5 mu, 2.87 mmol) and stirred at 40 °C for 16 hours. The reaction was diluted with ethyl acetate and water and the organic layer separated. The organic layer was washed with 1 N HCl, water (3 x 50 mL), and brine, then dried over Na2S04, filtered, and concentrated. The residue was slurried in dichloromethane to form a white precipitate. The precipitate was filtered and washed with dichloromethane to provide 4,5-dichloro-2-fluoro-N-(3-sulfamoylphenyl)benzamide (422 mg, 81percent) as a white powder. 1H NMR (400 MHz, DMSO-d6) delta 10.85 (s, 1H), 8.32 – 8.25 (m, 1H), 8.03 (d, J = 6.7 Hz, 1H), 7.93 (d, J = 9.5 Hz, 1H), 7.83 (dt, J = 6.8, 2.2 Hz, 1H), 7.64 – 7.52 (m, 2H), 7.42 (s, 2H) ppm. ESI-MS m/z calc. 361.96948, found 364.7 (M+l)+; Retention time: 1.4 minutes (3 minutes run).

The synthetic route of 98-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; HADIDA-RUAH, Sara Sabina; ANDERSON, Corey; TERMIN, Andreas P.; BEAR, Brian Richard; ARUMUGAM, Vijayalaksmi; KRENITSKY, Paul; JOHNSON, James Philip; WO2015/10065; (2015); A1;,
Amide – Wikipedia,
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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. 758-96-3, name is N,N-Dimethylpropionamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C5H11NO

General procedure: To a stirred solution of 46 (800 mg, 2.71 mmol) in THF (20 mL) was slowly added n-BuLi (1.58 mol/L in n-hexane; 3.90 mL, 6.16 mmol) at -78 C under an argon atmosphere. After stirring for 1 h at the same temperature, N,N-dimethylpropionamide (0.890 mL, 8.10 mmol) was added in one portion at -78 C and the reaction mixture was allowed to gradually warm to room temperature over 3 h. The reaction was quenched with satd NH4Cl aq and the resulting mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (CHCl3) to give 47 (342 mg, 1.26 mmol, 46%) as a white solid.

The synthetic route of 758-96-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ochiai, Koji; Takita, Satoshi; Eiraku, Tomohiko; Kojima, Akihiko; Iwase, Kazuhiko; Kishi, Tetsuya; Fukuchi, Kazunori; Yasue, Tokutaro; Adams, David R.; Allcock, Robert W.; Jiang, Zhong; Kohno, Yasushi; Bioorganic and Medicinal Chemistry; vol. 20; 5; (2012); p. 1644 – 1658;,
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Some common heterocyclic compound, 33045-52-2, name is Methyl 2-methoxy-5-sulfamoylbenzoate, molecular formula is C9H11NO5S, 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. COA of Formula: C9H11NO5S

EXAMPLE 23 N-(1-cyclopentyl-2-pyrrolidinyl-methyl)-2-methoxy-5-sulphamoyl-benzamide 23 g of methyl 2-methoxy-5-sulphamoyl benzoate (0.09 mole) is dissolved hot, at about 90 C., in 115 ml of glycol in a 500 ml flask fitted with an agitator and a thermometer. The solution is cooled to 50 C. and the ester re-crystallises. 19 g of 1-cyclopentyl-2-amino-methyl-pyrrolidine is added. The suspension obtained is kept at 50 C. After 30 hours the ester is completely dissolved. The solution continues to be heated until a sample taken is found to be completely soluble in acetic acid. The solution is then cooled and the benzamide crystallises slowly. 150 ml of water is added and the precipitate is drained, washed with water and dried. 23 g (68%) of benzamide is obtained with a melting point of 147-148 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33045-52-2, its application will become more common.

Reference:
Patent; Societe d’Etudes Scientifiques et Industrielle de l’Ile de France; US4673686; (1987); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics