HCID 178521019, compound → HCID 178479695, compound

Participants

Reaction Conditions

Reaction Steps

(R)-(1-(2-(1-(4-Chloro-1H-pyrazol-1-yl)cyclopropyl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (140 mg, Example 109-A) was dissolved in 0.5 mL acetone at 22° C. A one molar equivalent of concentrated (36% in water) HCl was added, drop wise, to the rapidly stirred solution. The sample immediately turned cloudy. Sample was warmed to 40° C. and an additional acetone (0.5 mL) was added. After about 30 minutes, the sample was cooled (˜1° C./min) to 22° C. White, opaque solids formed. The sample was vacuum filtered and the solids were collected/dried at room temperature (˜22° C.) to afford (R)-(1-(2-(1-(4-Chloro-1H-pyrazol-1-yl)cyclopropyl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone hydrochloride. 1H NMR (400 MHz, DMSO-d6) δ 1.43-2.01 (m, 12H), 2.60 (t, 1H), 2.92-3.10 (m, 2H), 3.29 (t, 2H), 3.38-3.46 (m, 1H), 3.46-3.56 (m, 1H), 4.26 (d, 1H), 4.32 (d, 1H), 7.04 (d, 1H), 7.72 (s, 1H), 7.82 (d, 1H), 8.32 (s, 1H).

Provenance & Evidence