Dichloromethane → HCID 86685338, compound

Participants

Reaction Steps

2-(3-(4-(7-(1-Methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-(trifluoromethylsulfonyl)azetidin-3-yl)acetonitrile (Example 96; 0.150 g, 0.305 mmol) was suspended in DCM (5 mL) and saturated aqueous NaHCO3 (2 mL). n-Chlorosuccinimide (0.204 g, 1.53 mmol) was added in one portion and the reaction mixture stirred at ambient temperature overnight. The reaction mixture was partitioned between saturated aqueous NaHCO3 and DCM. The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography, eluting with 2-3% (9:1 MeOH:NH4OH)/DCM to provide 2-(3-(4-(3-chloro-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-(trifluoromethylsulfonyl)azetidin-3-yl)acetonitrile (0.027 g, 0.051 mmol, 17% yield). MS (apci) m/z=526.0 (M+H).

Provenance & Evidence