Pyridine → HCID 58547120, compound

Participants

Reaction Steps

To a round bottomed flask was added 2-(3-(3-(1,4-diazepan-1-yl)pyrazin-2-yl)azetidin-1-yl)quinoline (0.0772 g, 0.214 mmol), pyridine (commercially available through Aldrich, 0.035 ml, 0.428 mmol), and 4-(pyrrolidin-1-yl)pyridine (commercially available through Alfa Aesar, 0.032 g, 0.214 mmol) and the reaction was allowed to stir at RT in DCM (0.714 ml). Methyl carbonochloridate (commercially available through Aldrich, 0.021 ml, 0.321 mmol) was added and allowed to stir overnight. Upon completion, the solvent was evaporated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage 50 g SNAP HP-silica column, eluting with a gradient of 0.5% to 5% MeOH in CH2CL2, to provide methyl 4-(3-(1-(quinolin-2-yl)azetidin-3-yl)pyrazin-2-yl)-1,4-diazepane-1-carboxylate (0.0632 g, 0.151 mmol, 70.5% yield). ESI-MS (M+1): 419.0. PDE10 IC50 (μM): 0.0046.

Provenance & Evidence