3-Aminopyridine → HCID 57874389, compound

Participants

Reaction Steps

DIPEA (156.8 mg, 1.2 mmol) followed by HOBt (45 mg, 0.33 mmol) and EDCI (116 mg, 0.6 mmol) were added to a stirred solution of [(1-pyridin-3-yl-1H-[1,2,3]triazole-4-carbonyl)-amino]-acetic acid (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) (75 mg, 0.3 mmol) in DMF (3 mL). After 2 minutes of stirring, 3-(piperidin-4-yloxy)-benzonitrile hydrochloride (prepared by the method used for the synthesis of Intermediate 15) (72.4 mg, 0.3 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was added and formed precipitate was collected. Purification by preparative HPLC afforded 15 mg (11.5% Yield) of 1-pyridin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid {2-[4-(3-cyano-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 432.19, 99.3%. 1H NMR (300 MHz, DMSO-d6): δ 9.5 (s, 1H), 9.22 (d, 1H), 8.8 (d, 1H), 8.58 (t, 1H), 8.44 (d, 1H), 7.7 (q, 1H), 7.58-7.44 (d, 2H), 7.44 (dd, 2H), 4.8 (m, 1H), 4.3 (d, 2H), 4.0 (bs, 1H), 3.8 (d, 1H), 2.5 (b, 2H), 2.1 (t, 2H), 1.7 (bd, 2H).

Provenance & Evidence