Cyclopentylamine → HCID 18446641, compound

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A solution of 3-(2-fluoro-4-pyridinyl)-2-(2-methyl-1,3-thiazol-4-yl)pyrazolo[1,5-a]pyridine (220 mg, 0.71 mmol) and potassium carbonate (98 mg, 0.71 mmol) in cyclopentylamine (5 mL) was heated at 100° C. for 12 days. After cooling to room temperature, the solution was diluted with ethyl acetate and the organic phase was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration, followed by flash chromatography (1:9 methanol/chloroform) gave N-cyclopentyl-4-[2-(2-methyl-1,3-thiazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyridinamine (265 mg, 100%) as an oil. 1H NMR (CDCl3): δ 8.49 (d, 1H), 8.04 (d, 1H), 7.49 (d, 1H), 7.08 (t, 1H), 6.74 (t, 1H), 6.59 (d, 1H), 6.43 (s, 1H), 5.44 (d, 1H), 3.79 (m, 1H), 2.73 (s, 3H), 1.92–1.42 (m, 8H). MS m/z 376 (M+1).

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