Hydrochloric Acid → HCID 57524507, compound

Participants

Reaction Steps

tert-Butyl 2-(4-((5-fluoropyridin-2-yl)methoxy)-2-oxopyridin-1(2H)-yl)-9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridine-6-carboxylate (0.14 g, 0.28 mmol) was treated with 1.25 M HCl in MeOH (7.0 mL), and the resulting suspension was stirred at ambient temperature for 18 h. The resulting solids were collected by filtration, dissolved in CH2Cl2 (30 mL), and washed with saturated NaHCO3 solution (50 mL). The resulting layers were separated, and the organic layer was dried over Na2SO4 and concentrated under reduced pressure to dryness. Flash chromatography (12 g ISCO column, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 4 column volumes, increased to 0:100 over 20 column volumes and held for 34 column volumes) provided the title compound (75 mg, 67%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 8.62 (d, J=2.7 Hz, 1H), 7.92-7.78 (m, 3H), 7.69-7.62 (m, 1H), 7.23 (d, J=8.1 Hz, 1H), 6.18 (dd, J=7.8, 2.7 Hz, 1H), 5.98 (d, J=2.7 Hz, 1H), 5.23 (s, 2H), 3.87 (s, 2H), 3.65 (s, 3H), 3.08 (t, J=5.7 Hz, 2H), 2.75 (t, J=5.4 Hz, 2H).

Provenance & Evidence