Cyclopentylamine → HCID 44234766, compound

Participants

Reaction Steps

DIPEA (300 mg, 2.3 mmol) was added to a stirred solution of 1-Cyclopentyl-1H-[1,2,3]triazole-4-carboxylic acid (75 mg, 0.41 mmol (prepared by the method used for the synthesis of Intermediate 64, starting from cyclopentylamine) in DMF (5 mL) followed by HOBt (61 mg, 0.4 mmol) and EDCI (200 mg, 1 mmol). After 2 minutes of stirring, 2-amino-1-[4-(5-chloro-pyridin-3-yloxy)-piperidin-1-yl]-ethanone hydrochloride (prepared according to Step 1 and 5 of the General Scheme) (156 mg, 0.5 mmol) was added and the resulting mixture was stirred at ambient temperature overnight. Cold water was then added and filtered the precipitate was filtered. The solid obtained was purified by recrystallisation from a solvent system EtOAc:hexane:MeOH (3:7:0.2) to afford 98 mg (55% Yield) of 1-cyclopentyl-1H-[1,2,3]triazole-4-carboxylic acid {2-[4-(5-chloro-pyridin-3-yloxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+ 433, 98.59%. 1H NMR (300 MHz, DMSO-d6): δ 8.7 (s, 1H), 8.34 (m, 2H), 8.24 (s, 1H), 7.74 (s, 1H), 5.1 (m, 1H), 4.9 (m, 1H), 4.2 (d, 2H), 4.0 (bs, 1H), 3.8 (bs, 1H), 3.4 (s, 1H), 3.3 (m, 1H), 2.3 (m, 2H), 2.1 (m, 4H), 1.9-1.5 (m, 6H).

Provenance & Evidence