Propanal → 2-(4-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-propylpiperidin-4-yl)acetonitrile

Participants

Reaction Steps

2-(4-(4-(7-(1-Methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)piperidin-4-yl)acetonitrile hydrochloride (Example 28, Step A; 30.0 mg, 0.0604 mmol) was suspended in acetonitrile (604 μL, 0.0604 mmol). To this was added triethylamine (33.7 μA, 0.242 mmol), followed by propionaldehyde (43.6 μL, 0.6043 mmol). After 30 minutes, NaBH(OAc)3 (64.0 mg, 0.302 mmol) was added. After stirring for 30 minutes, the reaction mixture was diluted in saturated sodium bicarbonate and EtOAc. The aqueous layer was back-extracted with DCM. The combined organic layers were washed with brine, dried with MgSO4, filtered and concentrated. Purification of the resulting crude material by reverse phase HPLC using a 0-100% acetonitrile/water gradient afforded afford 2-(4-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-propylpiperidin-4-yl)acetonitrile (7.0 mg, 23% yield). MS (apci) m/z=430.3 (M+H).

Provenance & Evidence