518057-72-2 Archives - Amides-buliding-blocks

September 23, 2021 News Simple exploration of 518057-72-2

The synthetic route of 518057-72-2 has been constantly updated, and we look forward to future research findings.

518057-72-2, name is 5-Amino-2-fluorobenzamide, 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. name: 5-Amino-2-fluorobenzamide

A solution of 5-amino-2-fluoro-benzamide (30 mg, 0.19 mmol) and diisopropylethylamine (100 mu, 0.5766 mmol) in tetrahydrofuran (1 mL) at 0 C was added to a slurry of 2-[2-methoxy-4- (trifluoromethoxy)phenoxy]-5-(l, l,2,2,2-pentafluoroethyl)benzoyl chloride (89 mg, 0.19 mmol) in tetrahydrofuran (1 mL) slowly at 0 C and the reaction was stirred at room temperature for 4 hours. The solvent was evaporated by blowing down with nitrogen. The crude product was dissolved in DMSO, filtered and purified by reverse phase HPLC to yield N-(3-carbamoyl-4-fluoro-phenyl)-2-[2-methoxy-4- (trifluoromethoxy)phenoxy]-5-(l, l,2,2,2-pentafluoroethyl)benzamide (25.7 mg, 23%). ESI-MS m/z calc. 582.08, found 583.0 (M+l)+; retention time (Method B): 2.04 minutes (3 minute run). NMR (400 MHz, DMSO-d6) delta 10.62 (s, 1H), 8.00 (dd, J = 6.5, 2.8 Hz, 1H), 7.91 (d, J = 2.4 Hz, 1H), 7.83 (ddd, J = 9.0, 4.4, 2.8 Hz, 1H), 7.78 – 7.62 (m, 3H), 7.44 (d, J = 8.8 Hz, 1H), 7.32 – 7.24 (m, 2H), 7.07 (ddd, J = 8.8, 2.8, 1.3 Hz, 1H), 6.87 (d, J = 8.8 Hz, 1H), 3.78 (s, 3H) ppm.

The synthetic route of 518057-72-2 has been constantly updated, and we look forward to future research findings.

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

New learning discoveries about C7H7FN2O

The synthetic route of 5-Amino-2-fluorobenzamide has been constantly updated, and we look forward to future research findings.

These common heterocyclic compound, 518057-72-2, name is 5-Amino-2-fluorobenzamide, 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. category: amides-buliding-blocks

To a solution of 5-amino-2-fluoro-benzamide (0.88 g, 5.7 mmol) and DIEA (3.0 mL, 17 mmol) in THF (20 mL) and dichloromethane (10 mL) at 0 C was added a solution of 6-cyclopropyl-4- [2-methoxy-4-(trifluoromethoxy)phenoxy]pyridine-3-carbonyl chloride (2.1 g, 5.4 mmol) in dichloromethane. The reaction mixture was removed from the ice bath and stirred at room temperature for 1 hour. The reaction mixture was diluted with water and extracted with dichloromethane. The organic layer was concentrated in vacuo and the resulting solid was purified using silica gel chromatography (0-60% ethyl acetate/hexanes) to provide N-(3 -carbamoyl -4-fluoro-phenyl)-6- cyclopropyl-4-[2-methoxy-4-(trifluoromethoxy)phenoxy]pyridine-3-carboxamide (1.1 g, 40%). ESI-MS m/z calc. 505.13, found 506.2 (M+l)+; retention time (Method B): 1.4 minutes (3 minute run). ‘H NMR (400 MHz, DMSO-d6) delta 10.41 (s, 1H), 8.55 (s, 1H), 7.99 (dd, J = 6.5, 2.8 Hz, 1H), 7.87 – 7.76 (m, 1H), 7.69 (d, J = 14.5 Hz, 2H), 7.45 (d, J = 8.8 Hz, 1H), 7.32 – 7.18 (m, 2H), 7.07 (ddd, J = 8.8, 2.8, 1.3 Hz, 1H), 6.59 (s, 1H), 3.80 (s, 3H), 2.07 (p, J = 6.7 Hz, 1H), 0.99 – 0.87 (m, 4H) ppm.

The synthetic route of 5-Amino-2-fluorobenzamide has been constantly updated, and we look forward to future research findings.

New learning discoveries about C7H7FN2O

The synthetic route of 5-Amino-2-fluorobenzamide has been constantly updated, and we look forward to future research findings.

Extended knowledge of C7H7FN2O

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.

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.

Sources of common compounds: 518057-72-2

The synthetic route of 518057-72-2 has been constantly updated, and we look forward to future research findings.

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. 518057-72-2, name is 5-Amino-2-fluorobenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-Amino-2-fluorobenzamide

To a well-stirred solution of 2-fluoro-5-aminobenzamide (43b)(0.20 g, 1.3 mmol) and 1-bromononane (0.30 g, 1.4 mmol) in ACN(20 mL) was added K2CO3 (0.25 g, 1.8 mmol). The reaction mixture was heated to reflux for 4 h. After the complete disappearance ofstarting material as indicated by TLC, the reaction mixture wassubjected to pass through a short pad of silica gel. The filtrate obtainedwas evaporated under reduced pressure and subjected topurification by flash column chromatography on silica gel. Thetitled compound (0.11 g) was obtained in 30% yield. 1H NMR(400 MHz, CDCl3) d 7.23e7.34 (m, 1H), 6.94 (d, J 8.8 Hz, 1H), 6.76(s, 1H), 6.62e6.71 (m, 1H), 6.28 (br. s., 1H), 3.70 (br. s., 1H), 3.11 (t,J 7.0 Hz, 2H),1.61 (quin, J 7.0 Hz, 2H),1.22e1.44 (m,12H), 0.89 (t,J 6.6 Hz, 3H); 13C NMR (101 MHz, CDCl3) d 165.6 (s, CONH2), 153.7(d, JCF 232 Hz, C2), 145.4 (d, JCF 2.0 Hz, C5), 120.1 (d, JCF 26 Hz,C1), 117.4 (d, JCF 9.1 Hz, C4), 116.5 (dd, JCF 12 Hz, C3), 114.3 (d,JCF 9.1 Hz, C6), 44.4, 31.9, 29.5, 29.4, 29.3, 27.1, 22.7, 14.1; LRMS(ESI) m/z 281 (M H, 100), 303 (M Na, 50); HRMS (ESI) calcdfor C16H26N2OF (M H) 281.2029, found 281.2033.

The synthetic route of 518057-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lui, Hok Kiu; Gao, Wei; Cheung, Kwan Choi; Jin, Wen Bin; Sun, Ning; Kan, Jason W.Y.; Wong, Iris L.K.; Chiou, Jiachi; Lin, Dachuan; Chan, Edward W.C.; Leung, Yun-Chung; Chan, Tak Hang; Chen, Sheng; Chan, Kin-Fai; Wong, Kwok-Yin; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 95 – 115;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some tips on 518057-72-2

Statistics shows that 5-Amino-2-fluorobenzamide is playing an increasingly important role. we look forward to future research findings about 518057-72-2.

Reference of 518057-72-2, These common heterocyclic compound, 518057-72-2, name is 5-Amino-2-fluorobenzamide, 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.

To 5-amino-2-fluoro-benzamide (70.54 mg, 0.4576 mmol) and diisopropylethylamine (178 mg, 1.37 mmol) in dichloromethane (2.4 mL) cooled at 0C was added dropwise a solution of 6-[2- chloro-4-(trifluoromethoxy)phenoxy]-2-fluoro-3-(trifluoromethyl)benzoyl chloride (200 mg, 0.46 mmol) in dichloromethane (2.4 mL). The reaction was stirred at room temperature overnight. The crude material was purified by silica gel chromatography (ethyl acetate/hexane gradient) to obtain N-(3- carbamoyl-4-fluoro-phenyl)-6- [2-chloro-4-(trifluoromethoxy)phenoxy] -2-fluoro-3 – (trifluoromethyl)benzamide (85 mg, 33%). ESI-MS m/z calc. 554.03, found 555.0 (M+l)+; retention time (Method B): 1.9 minutes (3 minute run). NMR (400 MHz, DMSO-d6) delta 11.06 (s, 1H), 7.98 (dd, J = 6.4, 2.8 Hz, 1H), 7.95 – 7.82 (m, 2H), 7.80 – 7.59 (m, 3H), 7.52 (d, J = 2.4 Hz, 2H), 7.30 (dd, J = 10.0, 9.1 Hz, 1H), 6.85 (d, J = 8.8 Hz, 1H) ppm.

Statistics shows that 5-Amino-2-fluorobenzamide is playing an increasingly important role. we look forward to future research findings about 518057-72-2.

Brief introduction of 518057-72-2

The synthetic route of 5-Amino-2-fluorobenzamide has been constantly updated, and we look forward to future research findings.

A mixture of 5-benzyloxy-2-fluoro-6-[4-(trifluoromethoxy)phenoxy]-3- (trifluoromethyl)benzoic acid (40 mg, 0.082 mmol), 5-amino-2-fluoro-benzamide (14 mg, 0.09 mmol), HATU (38 mg, 0.10 mmol) and DIPEA (50 mu, 0.2871 mmol) in DMF (700 mu was stirred at room temperature for 3 hours. The reaction mixture was quenched with water and the precipitated solid was filtered and washed with water. The solid was taken up in DCM, dried over MgSO/i, filtered and concentrated in vacuo. Product was purified by silica gel chromatography (0-50% ethyl acetate/hexanes) to afford 5-benzyloxy-N-(3-carbamoyl-4-fluoro-phenyl)-2-fluoro-6-[4-(trifluoromethoxy)phenoxy]-3- (trifluoromethyl)benzamide (28 mg, 52%). ESI-MS m/z calc. 626.11, found 627.2 (M+l)+; retention time (Method B): 2.09 minutes (3 minutes run). NMR (400 MHz, DMSO-d6) delta 11.01 (s, 1H), 7.89 (dd, J = 6.4, 2.8 Hz, 1H), 7.74 (d, J = 6.7 Hz, 1H), 7.71 – 7.63 (m, 3H), 7.36 – 7.18 (m, 6H), 7.09 – 7.04 (m, 2H), 6.97 – 6.92 (m, 2H), 5.17 (s, 2H) ppm.

The synthetic route of 5-Amino-2-fluorobenzamide has been constantly updated, and we look forward to future research findings.

Introduction of a new synthetic route about 518057-72-2

According to the analysis of related databases, 518057-72-2, the application of this compound in the production field has become more and more popular.

Electric Literature of 518057-72-2, 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 518057-72-2 as follows.

To 5-amino-2-fluoro-benzamide (37 mg, 0.24 mmol) and diisopropylethylamine (124 mu, 0.71 mmol) in dichloromethane (390 mu) cooled at 0 C was added dropwise a solution of 2-fluoro-6-(4- fluorophenoxy)-3-(trifluoromethyl)benzoyl chloride (80 mg, 0.24 mmol) in dichloromethane (390 mu). The reaction was stirred at room temperature for 1 hour. The solvent was evaporated and the residue was partitioned between water and ethyl acetate. The organic phase was concentrated to dryness. The residue was dissolved in 1ml of DMSO and purified by reverse phase HPLC to afford N-(3 -carbamoyl -4-fluoro- phenyl)-2-fluoro-6-(4-fluorophenoxy)-3-(trifluoromethyl)benzamide (25.5 mg, 24%). ESI-MS m/z calc. 454.08, found 455.1 (M+l)+; retention time (Method B): 1.63 minutes (3 minute run). l NMR (400 MHz, DMSO-d6) delta 11.05 (s, 1H), 7.98 (dd, J = 6.4, 2.8 Hz, 1H), 7.89 – 7.74 (m, 3H), 7.71 (s, 1H), 7.40 – 7.25 (m, 5H), 6.79 (d, J = 8.9 Hz, 1H) ppm.

According to the analysis of related databases, 518057-72-2, the application of this compound in the production field has become more and more popular.

Simple exploration of 518057-72-2

The synthetic route of 518057-72-2 has been constantly updated, and we look forward to future research findings.