3-Aminopyridine → HCID 57874373, compound

Participants

Reaction Steps

DIPEA (141 mg, 1.1 mmol) followed by HOBt (39 mg, 0.29 mmol) and EDCI (56 mg, 0.29 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) (67.5 mg, 0.27 mmol) in DMF (3 mL). After 2 minutes of stirring, 3-(2-chloro-phenoxy)-azetidine hydrochloride (prepared by the method used for the synthesis of Intermediate 71) (60 mg, 0.27 mmol) was added and the resulting mixture was stirred at room temperature overnight. The reaction mixture was partitioned between cold water and ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. Purification by preparative HPLC afforded 33 mg (29.4% Yield) of 1-pyridin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid {2-[3-(2-chloro-phenoxy)-azetidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 413, 98.7%. 1H NMR (300 MHz, DMSO-d6): δ 9.42 (s, 1H), 9.2 (d, 1H), 8.7 (m, 2H), 8.4 (m, 1H), 7.64 (m, 1H), 7.42 (m, 1H), 7.24 (m, 1H), 7.0 (t, 1H), 6.9 (d, 1H), 5.12 (m, 1H), 4.68 (m, 1H), 4.38 (m, 1H), 4.24 (m, 1H), 3.96 (m, 1H), 3.84 (m, 1H).

Provenance & Evidence