Chlorosuccinimide → HCID 68231181, compound

Participants

Reaction Steps

To a solution of 2-(3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-(2,2,2-trifluoro ethyl)azetidin-3-yl)acetonitrile (Example 71, 100 mg, 0.227 mmol) in DCM (1.5 mL) was added saturated NaHCO3 (1.0 mL) followed by N-chlorosuccinimide (46.3 mg, 0.340 mmol) in one portion. The biphasic mixture was vigorously stirred at ambient temperature for 17 hours and was diluted with DCM (2 mL). The solution was washed with H2O, dried over Na2SO4 and eluted through a silica gel plug (EtOAc elution). The solution was concentrated, the residual glass was dissolved in minimal DCM and hexane was added to afford a granular suspension. The suspension was concentrated and the residual solid was washed with warm 25% EtOAc/hexanes and dried in vacuum to afford the title compound (22 mg, 20% yield) as an ivory white powder. MS (apci) m/z=476.1 (M+H).

Provenance & Evidence