Hydrochloric Acid → (S)-1-(6-Fluoro-1-pyridin-3-yl-1H-benzoimidazol-2-yl)ethylamine

Participants

Reaction Conditions

Reaction Steps

A mixture of N—[(S)-1-(6-fluoro-1-pyridin-3-yl-1H-benzoimidazol-2-yl)ethyl]acetamide (126 mg) and 6N HCl (2 mL) was heated at 100° C. in a sealed vial for 1 h. After cooling to RT, the crude reaction mixture was partitioned between EtOAc and a saturated aqueous solution of NaHCO3. The organic fraction was washed with water, followed by brine, dried (Na2SO4) and concentrated in vacuo to afford 10 mg of crude material as an orange oil. The aqueous phase was re-extracted with DCM (×3) and the combined organic fractions were washed with brine, dried (Na2SO4) and concentrated in vacuo to afford 71 mg of crude material as a colourless oil. The crude materials were combined to afford the title compound as a pale orange oil (81 mg, 75%). 1H NMR (CDCl3, 400 MHz): δ 8.82 (1H, d, J=5.43 Hz), 8.75 (1H, s), 7.83 (1H, d, J=8.06 Hz), 7.73 (1H, dd, J=8.85, 4.75 Hz), 7.61-7.56 (1H, m), 7.06 (1H, t, J=9.26 Hz), 6.77 (1H, d, J=8.49 Hz), 4.14-4.04 (1H, m), 1.50 (3H, d, J=6.65 Hz)

Provenance & Evidence