Hydrochloric Acid → HCID 69813290, compound

Participants

Reaction Steps

A solution of (5R,7R)-4-(5-chloro-4-((isopropylamino)methyl)spiro[indoline-3,4′-piperidine]-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate (6 mg, 0.01 mmol) in THF (0.2 mL) was cooled to 0° C. and treated with 1N LiOH—H2O (0.020 mL, 0.020 mmol). The reaction was stirred at room temperature overnight. The reaction was partitioned between DCM and saturated aqueous NaHCO3 solution. The aqueous layer was extracted with DCM. The combined organic layers were washed with brine, dried, and concentrated. The crude residue was purified by column chromatography (10% 7N ammonia in MeOH/DCM) to yield the free base, which was taken up in DCM and acidified with 2N HCl in Et2O. The solvents were removed in vacuo. (5R,7R)-4-(5-chloro-4-((isopropylamino)methyl)spiro[indoline-3,4′-piperidine]-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol trihydrochloride (4 mg, 71%) was obtained as a solid. LCMS (APCI+) m/z 442, 444 [M+H]+; Rt=1.90 min.

Provenance & Evidence