Hydrochloric Acid → HCID 22181289, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of [3-(cyclopropylmethyl)-2-[(4-ethoxyphenyl)methyl]-3H-imidazo[4,5-b]pyridin-6-yl]-carbamic acid methyl ester (550 mg, 1.46 mmol) in dichloromethane (20 mL) at room temperature was added 1 M HCl in diethyl ether solution (3 mL). The mixture was stirred for 10 minutes and concentrated in vacuo. The residue was taken up into THE (5 mL) and diethyl ether (30 mL) and cooled to 0° C. LAH (137 mg, 3.61 mmol) was added to the solution. The mixture was stirred overnight. The reaction was then cooled to −78° C. and quenched with MeOH (3.20 mL) and water (3.20 mL). Na2SO4 was added to the mixture which was allowed to slowly warm up to room temperature. The mixture was filtered over Celite and concentrated in vacuo. The residue was purified using silica gel flash chromatography ([3.5% MeOH+0.5% NH4OH aq] in CH2Cl2) to provide 445 mg of the title compound 3-(cyclopropylmethyl)-2-[(4-ethoxyphenyl)methyl]-N-methyl-3H-imidazo[4,5-b]pyridin-6-amine (90.6% yield from [3-(cyclopropylmethyl)-2-[(4-ethoxyphenyl)methyl]-3H-imidazo[4,5-b]pyridin-6-yl]-carbamic acid methyl ester). 1H-NMR (400 MHz, CDCl3): δ 0.35 (m, 2H), 0.46 (m, 2H), 1.11 (m, 1H), 1.39 (t, J=7.0 Hz, 3H), 2.90 (s, 3H), 3.98 (m, 4H), 4.25 (s, 2H), 6.83 (d, J=8.8 Hz, 2H), 7.15 (d, J=8.8 Hz, 2H), 7.23 (d, J=2.5 Hz, 1H), 7.83 (d, J=2.5 Hz, 1H). MS (ESI) (M+H)+: 337.

Provenance & Evidence