HCID 86616863, compound → HCID 10118772, compound

Participants

Reaction Steps

A solution of methyl 6-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-(cyclopentylamino)pyrimidine-4-carboxylate (45 mg, 0.097 mmol) in cyclopentylamine (1 mL) was heated at 85° C. in a sealed tube for 24 hours. The reaction mixture was cooled and the excess cyclopentylamine was removed in vacuo. The resulting residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (4:1 hexanes:ethyl acetate) provided 6-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-cyclopentyl-2-(cyclopentylamino)pyrimidine-4-carboxamide (35 mg, 70%). 1H NMR (CDCl3) δ 8.34 (d, 1H), 7.78 (br, 1H), 7.65 (m, 2H), 7.31–7.26 (m, 2H), 7.14 (t, 2H), 7.07 (d, 1H), 5.16 (br, 1H), 4.34–4.24 (m, 2H), 2.07–2.00 (m, 4H), 1.80–1.48 (m, 12H); MS m/z 519 (M+1). A portion of this material was treated with anhydrous hydrochloric acid in ether to provide a hydrochloride salt as a yellow solid.

Provenance & Evidence