Cyclopentylamine → HCID 10288486, compound

Participants

Reaction Conditions

Reaction Steps

To 4-[7-chloro-2-(2-methyl-1,3-thiazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyridinamine from previous reaction was added cyclopentylamine and the resulting mixture heated to 80° C. for 3 days. The resultant solution was cooled to room temperature, diluted with ethyl acetate and washed with water, brine and dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (1:19 methanol/dichloromethane) gave N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyridinyl]-2-(2-methyl-1,3-thiazol-4-yl)pyrazolo[1,5-a]pyridin-7-amine (20 mg, 120% for two steps) as a brown foam. 1H NMR (CDCl3): δ 8.09 (d, 1H), 7.56 (d, 1H), 7.34 (s, 1H), 7.15 (t, 1H), 6.98 (d, 1H), 6.64 (d, 1H), 6.45 (s, 1H), 5.60 (d, 1H), 4.80 (b, 1H), 3.94 (m, 1H), 3.87 (m, 1H), 2.76 (s, 3H), 1.98–1.45 (m, 16H). MS m/z 459 (M+1).

Provenance & Evidence