Hydrochloric Acid → HCID 10184476, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-{7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}benzonitrile (50 mg, 0.1 mmol) in methanol was added 4N potassium hydroxide. After heating at 85° C. for 2 days, the reaction mixture was cooled to room temperature and acidified with 2N hydrochloric acid. The solution was extracted with ethyl acetate. The organic phases were combined and dried over magnesium sulfate. Filtration and concentration, followed by purification by flash chromatography (90:10 ethyl acetate:methanol) gave 3-{7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}benzoic acid (10 mg, 19%) as a brown foam. 1H NMR (CDCl3): δ 8.11 (s, 1H), 8.00 (d, 1H), 7.96 (d, 1H), 7.80 (broad s, 1H), 7.64 (d, 1H), 7.46 (t, 1H), 7.37 (t, 1H), 6.98 (d, 1H), 6.57 (d, 1H), 6.21 (d, 1H), 6.11 (broad, 1H), 4.12 (m, 1H), 4.01 (m, 1H), 2.06 (m, 2H), 1.88 (m, 2H), 1.69–1.49 (m, 12H). MS m/z 483 (M+1); 481 (M−1).

Provenance & Evidence