Cyclopentylamine → HCID 22180919, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[7-chloro-2-(4-fluorophenyl)-6-(triethoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (2.37 g, 4.28 mmol) and cyclopentylamine (10 mL, 100 mmol) was heated in a sealed tube at 80° C. for 16 hours. The reaction mixture was cooled to room temperature and excess cyclopentylamine was removed in vacuo. The crude solid was triturated in water. The solids were collected on a filter to provide N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-6-(triethoxymethyl)pyrazolo[1,5-a]pyridin-7-amine (2.48 g, 96%). Rf 0.42 (4:1 hexanes:ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 8.04 (d, 1H), 7.75 (d, 1H), 7.68–7.60 (m, 3H), 7.12 (t, 2H), 6.36–6.31 (m, 2H), 5.30 (m, 1H), 5.07 (d, 1H), 4.53 (m, 1H), 3.45 (q, 6H), 2.12–1.95 (m, 4H), 1.80–1.45 (m, 12H), 1.25 (t, 9H); MS m/z 603 (M+1).

Provenance & Evidence