(3-Nitro-pyridin-4-yl)-{4-[4-(3-pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-amine → N*4*-{4-[4-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-pyridine-3,4-diamine

Participants

Reaction Steps

A solution of (3-Nitro-pyridin-4-yl)-{4-[4-(3-pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-amine (200 mg, 0.45 mmol) in ethanol (˜5 mL) was hydrogenated for 4 hours at room temperature at 40 psi in the presence of 10% Pd/C (20 mg, 10% w/w). The reaction mixture was filtered over Arbocel® and rinsed with ethanol. The filtrate was concentrated in vacuo to give a brown oily residue. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (94:6:0.6, by volume) to provide the title compound (68 mg, 36%). HRMS ESI+ m/z 411.2750 [MH]+.

Provenance & Evidence