Hydrochloric Acid → HCID 66823780, compound

Participants

Reaction Steps

A mixture of bis(1,1-dimethylethyl) (7-cyano-3-{1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}furo[3,2-c]pyridin-4-yl)imidodicarbonate (359 mg, 3:2 mixture with non-Boc as described above) and 4.0 M HCl in dioxane (3.0 mL, 12.00 mmol) was stirred at room temperature under Nitrogen for 14 hr. The mixture was concentrated in vacuo and taken up in EtOAc (50 mL) and saturated aqueous sodium bicarbonate (50 mL). The layers were separated and the aqueous layer was extracted with EtOAc (50 mL). The combined organic layers were washed with brine (1×50 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography (Analogix, 40 g SiO2, 15%-85% EtOAc in hexanes gradient over 52 minutes) to give 4-amino-3-{1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}furo[3,2-c]pyridine-7-carbonitrile (118 mg, 45.7% yield) as a white solid. LC/MS (ES) m/z=431 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 3.28 (t, 2H), 3.97 (s, 2H), 4.30 (t, J=8.46 Hz, 2H), 6.57 (br. s., 2H), 7.14-7.33 (m, 4H), 7.40 (s, 1H), 8.09-8.17 (m, 2H), 8.38 (s, 1H).

Provenance & Evidence