3-AMINO-5-CHLOROPYRIDINE-2-CARBOXAMIDE

To a suspension of 5-chloro-2-cyano-3-nitropyridine (1.274 mL, 10.9 mmol) in water (22 mL) was added 28% aqueous ammonium hydroxide (3.94 mL, 28.3 mmol), and the reaction was stirred at RT for 20 minutes. Sodium hydrosulfite (2.68 mL, 32.7 mmol) was added, and the reaction mixture was stirred at RT for 70 minutes. The yellow precipitate was collected by vacuum filtration to provide the title compound (1.097 g, 6.39 mmol) as yellow solid. 1H-NMR (400 MHz, DMSO-d6): delta 7.88 (br. s, 1H), delta 7.73 (s, 1H), delta 7.39 (br. s, 1H), delta 7.23 (s, 1H), delta 7.06 (br. s, 2H). LC/MS (ESI+) m/z=172 (M+H)To a suspension of 5-chloro-2-cyano-3-nitropyridine (1.274 mL, 10.9 mmol) in water (22 mL) was added 28%o aqueous ammonium hydroxide (3.94 mL, 28.3 mmol), and the reaction was stirred at RT for 20 minutes. Sodium hydrosulfite (2.68 mL, 32.7 mmol) was added, and the reaction mixture was stirred at RT for 70 minutes. The yellow A-1813-WO-PCT - 145 - precipitate was collected by vacuum filtration to provide the title compound (1.097 g, 6.39 mmol) as yellow solid. H-NMR (400 MHz, DMSO-i): delta 7.88 (br. s, 1 H), delta 7.73 (s, 1 H), delta 7.39 (br. s, 1 H), delta 7.23 (s, 1 H), delta 7.06 (br. s, 2 H). LC/MS (ESI+) m/z = 172 (M+H)+To a suspension of 5-chloro-2-cyano-3-nitropyridine (1.274 mL, 10.9 mmol) in water (22 mL) was added 28% aqueous ammonium hydroxide (3.94 mL, 28.3 mmol), and the reaction was stirred at RT for 20 minutes. Sodium hydrosulfite (2.68 mL, 32.7 mmol) was added, and the reaction mixture was stirred at RT for 70 minutes. The yellow precipitate was collected by vacuum filtration to provide the title compound (1.097 g, 6.39 mmol) as yellow solid. 1H-NMR (400 MHz, DMSO-d6): delta 7.88 (br. s, 1H), delta 7.73 (s, 1H), delta 7.39 (br. s, 1H), delta 7.23 (s, 1H), delta 7.06 (br. s, 2H). LC/MS (ESI+) m/z=172 (M+H).To a suspension of 5-chloro-2-cyano-3-nitropyridine (1.274 mL, 10.9 mmol) in water (22 mL) was added 28% aqueous NH4OH (3.94 mL, 28.3 mmol), and the reaction was stirred at RT for 20 min. Sodium hydrosulfite (2.68 mL, 32.7 mmol) was added, and the reaction mixture was stirred at RT for 70 minutes. The yellow precipitate was collected by vacuum filtration to provide the title compound (1.097 g, 6.39 mmol) as yellow solid. 1H-NMR (400 MHz, DMSO-d6): delta 7.88 (br. s, 1 H), delta 7.73 (s, 1 H), delta 7.39 (br. s, 1 H), delta 7.23 (s, 1 H), delta 7.06 (br. s, 2 H). LC/MS (ESI+) m/z = 172 (M+H) +.3-Amino-5-chloropicolinamide (12.1 g, 70.5 mmol) was added to 300 mL of triethyl orthoformate and the resulting solution was stirred at 130 C for 2 days. After cooled to room temperature, the precipitated solid was collected by filtration and the filter cake was washed with ethyl acetate and dried in vacuo to give 11.4 g (89%) of the title compound as a grey solid. MS (ESIpos): m/z = 182 (M+H)+. LC-MS [Method 2]: R, = 0.55 min.3-Amino-5-chloropicolinonitrile (25 g, 162.8 mmol) was added 80 mL of concentrated sulfuric acid and the resulting mixture was stirred at 80C for 4 hours. After cooled to room temperature, the resulting mixture was poured into ice cold water and the pH value was adjusted to 12 with saturated sodium hydroxide solution. The precipitated solid was collected by filtration and the filter cake was washed with water and dried in vacuo to give 19 g (77%) of the title compound as a yellow solid. MS (ESIpos): m/z = 172 (M+H)+. LC-MS [Method 2]: R, = 0.75 min.

Molecular Weight:171.58
XLogP3:0.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:171.0199395
Monoisotopic Mass:171.0199395
Topological Polar Surface Area:82
Heavy Atom Count:11
Complexity:164
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes