Acetic Anhydride → 2-Methyl-1-{4-[4-(3-pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-1h-imidazo[4,5-c]pyridine

Participants

Reaction Steps

N*4*-{4-[4-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-pyridine-3,4-diamine (60 mg, 0.15 mmol) and acetic anhydride (˜1 mL) were stirred at reflux for 18 hours. The reaction mixture was quenched with ˜1 mL water, then basified with dilute sodium carbonate solution then extracted with DCM (2×20 mL). The organics were combined, dried over sodium sulphate, filtered and concentrated in vacuo to give a brown oil. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:5:0.5 to 90:10:1 by volume) to provide the title compound as a brown oil (19 mg, 30%). 1H NMR (400 MHz, CDCl3) δ 1.78-1.82 (m, 6H), 1.97-2.10 (m, 5H), 2.23 (m, 2H), 2.54 (m, 4H), 2.62 (t, 2H), 3.40 (m, 2H), 3.82 (m, 2H), 4.00 (t, 2H), 4.07 (s, 2H), 6.80-6.88 (m, 4H), 7.00 (d, 1H), 8.30 (d, 1H), 8.92 (s, 1H). LRMS ESI+ m/z 435 [MH]+.

Provenance & Evidence