Acetonitrile → 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

Participants

Reaction Conditions

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)azetidin-3-yl)acetonitrile hydrochloride (Example 62; 50 mg, 0.12 mmol) in acetonitrile (1.2 mL, 0.12 mmol) was added K2CO3 (48 mg, 0.35 mmol) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (30 mg, 0.13 mmol). The reaction mixture was heated to 45° C. for 15 hours, then cooled. After diluting in water, the mixture was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. Purification of the crude material by reverse phase HPLC using a 0-100% acetonitrile/water gradient afforded 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 (24 mg, 48.0% yield). MS (apci) m/z=442.2 (M+H).

Provenance & Evidence