HCID 17953061, compound → HCID 10115190, compound

Participants

Reaction Steps

A solution of N-cyclopentyl-2-(4-fluorophenyl)-3-(2-fluoro-4-pyridinyl)pyrazolo[1,5-α]pyridin-7-amine (37 mg, 0.10 mmol) in cyclopentylamine (4 mL) was heated to 150° C. in a sealed tube for 12 hours. Upon cooling to room temperature, the mixture was concentrated in vacuo and the residue was taken up in ether and washed with water and then brine. The aqueous layer was extracted with ether and the combined organics were dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (4:1 to 2:1 hexanes:ethyl acetate) provided N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyridinyl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-7-amine (31 mg, 72%) as a solid. 1H NMR (CDCl3): δ 8.01 (d, 1H), 7.64 (dd, 2H), 7.21 (t, 1H), 7.10–7.02 (m, 3H), 6.57 (d, 1H), 6.34 (s, 1H), 6.01 (d, 1H), 5.97 (d, 1H), 4.63 (broad, 1H), 4.02 (m, 1H), 3.79 (m, 1H), 2.16 (m, 2H), 1.96–1.42 (m, 14H); 19F NMR (CDCl3) δ −114.06; MS m/z 456 (M+1).

Provenance & Evidence