Tetrahydrofuran → HCID 58869558, compound

Participants

Reaction Steps

A solution of 4-[2-(4-Fluorophenyl)-8-methylimidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylpiperidin-4-ylamine (Example #H.1.1; 0.2 g, 0.5 mmol) in THF (1.1 mL, 1.4 mmol) was cooled to about 0° C. Then TEA (0.13 mL, 0.94 mmol) was added followed by acetic acid chlorocarbonylmethyl ester (0.077 g, 0.56 mmol). After about 16 h, the mixture was allowed to warm to ambient temperature and filtered, washing with MeOH. The filtrate was treated with 2.50 M aqueous sodium hydroxide (0.20 mL) at ambient temperature. After about 16 h, the mixture was treated with additional 2.50 M aqueous sodium hydroxide (0.16 mL). After about 6 h, the mixture was acidified to pH 5 using 1 N HCl. The mixture was treated with DCM and water, and the layers were separated. The aqueous layer was washed with DCM (3×20 mL). The combined organic layers were dried over MgSO4 and concentrated. The crude material was taken up in DCM/MeOH and purified via FCC using DCM/2.5% NH4OH in MeOH (95:5) to yield the title compound as a white solid after drying (0.115 g, 50%): LC/MS (Table 1, Method b) Rt=1.6 min; MS m/z: 462.3 (M+H)+.

Provenance & Evidence