Cyclopentylamine → HCID 10277523, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[7-chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-5,6-dimethyl-2-pyrimidinamine (80 mg, 0.19 mmol) and cyclopentylamine (2 mL, 20 mmol) was heated in a sealed tube at 90° C. for 3 hours followed by 125° C. for 24 hours. The reaction mixture was cooled to room temperature and excess cyclopentylamine was removed in vacuo. The crude residue was washed with saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted with ethyl acetate. The combined extracts were washed with water and brine then dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (5:1 hexanes:ethyl acetate) provided N-cyclopentyl-3-[2-(cyclopentylamino)-5,6-dimethyl-4-pyrimidinyl]-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-7-amine (40 mg, 44%) as a clear oil. Rf 0.32 (4:1 hexanes:ethyl acetate); 1H NMR (CDCl3) δ 7.57 (s, 1H), 7.33 (d, 1H), 7.19–7.11 (m, 3H), 6.91 (d, 1H), 6.03 (d, 1H), 6.93 (d, 1H), 4.91 (d, 1H), 4.29 (m, 1H), 4.01 (m, 1H), 2.34 (s, 3H), 2.28 (s, 3H), 2.15 (m, 2H), 1.99 (broad, 2H), 1.87–1.40 (m, 15H); MS m/z 481 (M+1). To a solution of the product (20 mg) in ether was added 1 M HCl in ether. The precipitated solid was isolated to give the corresponding HCl salt.

Provenance & Evidence