Category: 75903-58-1

Synthetic Route of 75903-58-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 75903-58-1, name is 6-Aminopyridine-2-sulfonamide, molecular formula is C5H7N3O2S, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

[001308] 2-Chloro-6-(3-fluoro-5-isobutoxy-phenyl)pyridine-3-carboxylic acid (3.00 g, 9.27 mmol) was dissolved in N,N-dimethylformamide (30.00 mL), and 1,1?- carbonyldiimidazole (2.254 g, 13.90 mmol) was added to the solution. The solution was allowed to stir at 65 C for 1 hour. In a separate flask, sodium hydride (444.8 mg, 11.12 mmol) was added to a solution of 6-aminopyridine-2-sulfonamide (1.926 g, 11.12 mmol) in N,N-dimethylformamide (15.00 mL). This mixture was stirred for one hour before being added to the prior reaction mixture. The final reaction mixture was stirred at 65 C for 15 minutes. Volatiles were removed under reduced pressure. The remaining oil was taken up in ethyl acetate and washed with aqueous hydrochloric acid (1 N, 1 × 75 mL) and brine (3 × 75 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The remaining white solid (4.7 g) was fully dissolved in isopropanol (120 mL) in an 85 C water bath. The colorless solution was allowed to slowly cool to room temperature with slow stirring over 16 hours. The crystalline solids that had formed were collected by vacuum filtration, and then rinsed with cold isopropanol (50 mL). Upon drying, N-[(6-amino-2- pyridyl)sulfonyl]-2-chloro-6-(3-fluoro-5-isobutoxy-phenyl)pyridine-3-carboxamide (3.24 g, 6.76 mmol, 73%) was obtained as a white solid. 1H NMR (400 MHz, DMSO- d6) delta 12.78 (s, 1H), 8.15 (d, J = 8.0 Hz, 1H), 8.09 (d, J = 7.9 Hz, 1H), 7.73 – 7.63 (m, 1H), 7.49 (dd, J = 8.6, 1.9 Hz, 2H), 7.21 (d, J = 7.3 Hz, 1H), 6.99 (dt, J = 10.7, 2.2 Hz, 1H), 6.74 (d, J = 8.4 Hz, 1H), 6.64 (s, 2H), 3.86 (d, J = 6.5 Hz, 2H), 2.05 (dp, J = 13.3, 6.5 Hz, 1H), 1.02 (dd, J = 12.7, 6.4 Hz, 6H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 75903-58-1, 6-Aminopyridine-2-sulfonamide.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; BEAR, Brian; CLEMENS, Jeremy; CLEVELAND, Thomas; COON, Timothy, Richard; GROOTENHUIS, Peter, Diederik Jan; FRIEMAN, Bryan, A.; HADIDA RUAH, Sara S.; KHATUYA, Haripada; KRENITSKY, Paul, J.; MILLER, Mark, Thomas; SILINA, Alina; UY, Johnny; ZHOU, Jinglan; (528 pag.)WO2017/173274; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 75903-58-1, name is 6-Aminopyridine-2-sulfonamide, the common compound, a new synthetic route is introduced below. COA of Formula: C5H7N3O2S

6-(3-fluoro-5-isobutoxy-phenyl)-2-(3,5,5-trimethylcyclopenten-1-yl)pyridine-3-carboxylic acid (74 mg, 0.19 mmol) and CDI (45 mg, 0.28 mmol) were mixed in DMF (740 muL) under and atmosphere of nitrogen and the reaction mixture was heated to 45 C. for 45 minutes. In a separate vial, 6-aminopyridine-2-sulfonamide (80.62 mg, 0.4655 mmol) and NaH (18 mg, 0.46 mmol) were mixed slowly in DMF (370.0 muL) and mixture was heated to 45 C. for 45 minutes. The 6-aminopyridine-2-sulfonamide reaction mixture was added to the activated acid and the reaction mixture was heated at 50 C. for 16 h. The reaction mixture was filtered and then purified directly by reverse-phase preparative chromatography utilizing a C18 column and HPLC-MS method 10-99% mobile phase B (mobile phase A=water (de-ionized, no acid modifier), mobile phase B=acetonitrile) to afford N-[(6-amino-2-pyridyl)sulfonyl]-6-(3-fluoro-5-isobutoxy-phenyl)-2-(3,5,5-trimethylcyclopenten-1-yl)pyridine-3-carboxamide (Compound 2081) (Compound 2039) (64 mg, 62%) as an off-white solid, ESI-MS m/z calc. 552.22064. found 553.4 (M+1)+. Retention time: 2.25 minutes; 1H NMR (400 MHz, DMSO) delta 12.55 (s, 1H), 7.96 (d, J=8.2 Hz, 1H), 7.86 (d, J=8.2 Hz, 1H), 7.68-7.60 (m, 1H), 7.56 (s, 1H), 7.49 (d, J=9.6 Hz, 1H), 7.20 (d, J=7.3 Hz, 1H), 7.01-6.84 (m, 1H), 6.72 (d, J=8.4 Hz, 1H), 6.55 (s, 2H), 5.62 (d, J=1.7 Hz, 1H), 3.85 (d, J=6.6 Hz, 2H), 2.66 (ddd, J=14.3, 7.4, 1.8 Hz, 1H), 2.03 (dd, J=13.2, 6.6 Hz, 1H), 1.95 (dd, J=12.1, 7.5 Hz, 1H), 1.38-1.28 (m, 4H), 1.25 (s, 3H), 0.99 (d, J=6.7 Hz, 6H), 0.93 (d, J=6.9 Hz, 3H).

The synthetic route of 75903-58-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; Miller, Mark Thomas; Anderson, Corey; Arumugam, Vijayalaksmi; Bear, Brian Richard; Binch, Hayley Marie; Clemens, Jeremy J.; Cleveland, Thomas; Conroy, Erica; Coon, Timothy Richard; Frieman, Bryan A.; Grootenhuis, Peter Diederik Jan; Gross, Raymond Stanley; Hadida-Ruah, Sara Sabina; Haripada, Khatuya; Joshi, Pramod Virupax; Krenitsky, Paul John; Lin, Chun-Chieh; Marelius, Gulin Erdgogan; Melillo, Vito; McCartney, Jason; Nicholls, Georgia McGaughey; Pierre, Fabrice Jean Denis; Silina, Alina; Termin, Andreas P.; Uy, Johnny; Zhou, Jinglan; (590 pag.)US2016/95858; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 75903-58-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 75903-58-1, name is 6-Aminopyridine-2-sulfonamide, molecular formula is C5H7N3O2S, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 225 (2S,3R,4S,5S)-N-(6-aminopyridine-2-sulfonyl)-3-tert-butyl-4-[(5-cyclobutyl-2-methoxypyridin-3-yl)methoxy]-5-(2-cyclopropylphenyl)-1-[(2S)-oxane-2-carbonyl]pyrrolidine-2-carboxamide (2S,3R,4S,5S)-3-(tert-Butyl)-4-((5-cyclobutyl-2-methoxypyridin-3-yl)methoxy)-5-(2-cyclopropylphenyl)-1-((S)-tetrahydro-2H-pyran-2-carbonyl)pyrrolidine-2-carboxylic acid (Example 171B) (48.8 mg, 0.083 mmol) and di(1H-imidazol-1-yl)methanone (20.09 mg, 0.124 mmol) were combined in N,N-dimethylformamide (1 mL) and warmed to 65 C. for 1 hour. 6-Aminopyridine-2-sulfonamide (14.31 mg, 0.083 mmol) was dissolved in 0.3 mL of N,N-dimethylformamide and sodium hydride (3.47 mg, 0.087 mmol) (60% dispersion in mineral oil) was added in portions. The reaction was stirred at ambient temperature for one hour, the mixture was added to the NaH/sulfonamide suspension and the resulting mixture was stirred at ambient temperature for 16 hours. The solvent was reduced in volume and the crude material was quenched with water and 1N aqueous HCl was added dropwise to acidic pH. The resulting precipitate was filtered and washed with water. The crude precipitate was purified by reverse-phase preparative HPLC on a Phenomenex Luna C8(2) 5 mum 100 A AXIA column (30 mm*150 mm). A gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B) was used, at a flow rate of 50 mL/minute (0-0.5 minutes 10% A, 0.5-7.0 minutes linear gradient 10-95% A, 7.0-10.0 minutes 95% A, 10.0-12.0 minutes linear gradient 95-10% A) to provide the title compound as the trifluoroacetic acid salt. 1H NMR (400 MHz, DMSO-d6) delta ppm 7.74 (d, J=2.5 Hz, 1H), 7.63 (dd, J=7.5, 1.7 Hz, 1H), 7.44 (dd, J=8.3, 7.3 Hz, 1H), 7.13 (dd, J=7.3, 0.9 Hz, 1H), 7.11-7.04 (m, 2H), 6.94 (dd, J=7.5, 1.6 Hz, 1H), 6.78 (d, J=2.4 Hz, 1H), 6.64 (dd, J=8.4, 0.8 Hz, 1H), 5.89 (d, J=6.1 Hz, 1H), 4.57 (d, J=2.6 Hz, 1H), 4.31 (dd, J=6.1, 1.7 Hz, 1H), 4.23 (d, J=13.4 Hz, 1H), 3.95 (d, J=9.0 Hz, 1H), 3.91 (s, 1H), 3.77 (s, 1H), 3.74 (s, 3H), 3.69-3.56 (m, 1H), 3.33-3.27 (m, 3H), 2.55 (t, J=2.2 Hz, 1H), 2.27-2.13 (m, 2H), 2.04-1.79 (m, 4H), 1.71-1.62 (m, 1H), 1.54-1.43 (m, 1H), 1.36 (dt, J=8.8, 4.3 Hz, 2H), 1.22-1.07 (m, 1H), 1.00 (s, 9H), 0.96-0.82 (m, 2H), 0.71 (ddd, J=9.1, 5.5, 3.8 Hz, 1H), 0.46 (ddd, J=9.5, 6.4, 3.7 Hz, 1H); MS (APCI+) m/z 746 (M+H)+.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 75903-58-1, 6-Aminopyridine-2-sulfonamide.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Desroy, Nicolas; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Scanio, Marc J.; Searle, Xenia; Wang, Xueqing; Yeung, Ming C.; Zhao, Gang; (247 pag.)US2018/99932; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem