Hydrochloric Acid → N-[((1S,2S,4R)-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-hydroxycyclopentyl)methyl]-N-methylsulfamide

Participants

Reaction Steps

N-[((1S,2S,4R)-2-[tert-Butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methyl]-N-methylsulfamide (25.0 mg, 0.0000438 mol) was dissolved in tetrahydrofuran (2.0 mL), ethanol (2.0 mL) and 1.00 M of hydrochloric acid in water (2.0 mL). The mixture was stirred overnight at room temperature. The solution was evaporated to dryness, and the residue was dissolved in methanol and treated with a 7.00 M solution of ammonia in methanol (0.1 mL). Solvents were again evaporated, and the residue was purified by silica gel chromatography, eluting with 2 to 10% methanol in dichloromethane to yield the product, 9.8 mg (49%). 1H-NMR (400 MHz, MeOD) δ 8.16 (s, 1H), 7.19 (m, 5H), 6.62 (d, 1H, J=3.6 Hz), 5.84 (t, J=7.7 Hz, 1H), 5.43 (ddd, J=4.5 Hz, 8.6 Hz, 12.8 Hz, 1H), 4.43 (t, J=3.7 Hz, 1H), 3.25 (dd, J=8.1 Hz, 13.7 Hz, 1H), 3.14 (dd, J=7.2 Hz, 13.7 Hz, 1H), 3.05 (ddd, J=3.3 Hz, 8.8 Hz, 15.8 Hz, 1H), 2.91 (m, 1H), 2.74 (m, 1H, 2.63 (m, 1H), 2.34 (ddd, J=1.1 Hz, 7.8 Hz, 13.6 Hz, 1H), 2.20 (m, 2H, 1.99 (m, 2H). LC/MS: Rt=1.51 min, ES+ 457 (AA standard).

Provenance & Evidence