3-Aminopyridine → HCID 44235022, compound

Participants

Reaction Steps

DIPEA (94.1 mg, 0.72 mmol) was added to a stirred solution of [(1-pyridin-3-yl-1H-[1,2,3]triazole-4-carbonyl)-amino]-acetic acid (45 mg, 0.18 mmol) (prepared by the method used for the synthesis of Intermediate 64, starting from 3-aminopyridine, and subsequently, application of Step 3 of the General Scheme) in DMF (2 mL) followed by HOBt (27 mg, 0.2 mmol) and EDCI (69.8 mg, 0.366 mmol). After 2 minutes of stirring, 4-methyl-3-(piperidin-4-yloxy)-benzonitrile hydrochloride (prepared by the method used for the synthesis of Intermediate 15) (50.6 mg, 0.2 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was added and the precipitate was collected. The solid was purified by stirring in mixture of DCM in hexane to afford 40 mg (49.2% Yield) of 1-pyridin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid {2-[4-(5-cyano-2-methyl-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 446.19, 96.84%. 1H NMR (300 MHz, DMSO-d6): δ 9.45 (s, 1H), 9.2 (d, 1H), 8.75 (d, 1H), 8.55-8.45 (t, 1H), 8.4 (m, 1H), 7.72-7.64 (m, 1H), 7.55 (s, 1H), 7.4-7.3 (q, 2H), 4.8 (m, 1H), 4.25 (d, 2H), 3.8-3.6 (m, 2H), 3.5-3.4 (m, 2H), 2.25 (s, 3H), 2.1-1.8 (m, 2H), 1.8-1.5 (m, 2H).

Provenance & Evidence