Hydrochloric Acid → HCID 10184686, compound

Participants

Reaction Steps

To a solution of N-cyclopentyl-3-{2-(cyclopentylamino)-6-[(tetrahydro-2H-pyran-2-yloxy)methyl]-4-pyrimidinyl}-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-7-amine (134 mg, 2.23 mmol) in tetrahydrofuran (8 mL) was added hydrochloric acid (4 mL, 4 N aqueous, 32 mmol). After 30 minutes, the solution was made basic with sodium bicarbonate and ether was added. The organic layer was washed with water and brine and dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (2:1 to 1:1 hexanes:ethyl acetate) provided {2-(cyclopentylamino)-6-[7-(cyclopentylamino)-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-4-pyrimidinyl}methanol (80 mg, 71%). This material was taken up in ether and treated with anhydrous hydrochloric acid in ether to yield upon filtration a yellow solid. 1H NMR of hydrochloride salt (CDCl3) δ 8.00–7.94 (broad, 1H), 7.78 (d, 1H), 7.54–7.44 (m, 3H), 7.17 (m, 2H), 6.22 (s, 1H), 6.19 (d, 1H), 6.07 (d, 1H), 4.74–4.60 (broad, 1H), 4.47 (s, 2H), 4.36 (m, 1H), 3.99 (m, 1H), 2.16–2.00 (m, 4H), 1.82–1.59 (m, 12H); 19F NMR (CDCl3) δ −111.26; MS m/z 487 (M+1 of free base).

Provenance & Evidence