Hydrochloric Acid → Hydrochloric Acid

Participants

Reaction Steps

Concentrated HCl (5 mL) was added to 1-((3aS,4R,6aR)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-7-fluoro-1H-imidazo[4,5-c]pyridin-4-amine (1-7) (2.3 g, 7.9 mmol, 1 equiv) in methanol (60 mL). After disappearance of the starting material as monitored by LC-MS analysis, the mixture was concentrated to afford (1R,2S,3R)-3-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)cyclopentane-1,2-diol (1-9) as a tan solid of the bis-HCl salt. 1H NMR (1-9) (500 MHz, DMSO): δ 8.76 (s, 1H); 8.55 (s, 2H); 8.03 (d, J=5.5 Hz, 1H); 4.88 (q, J=9.3 Hz, 1H); 4.19 (dd, J=9.4, 4.0 Hz, 1H); 4.00 (t, J=4.5 Hz, 1H); 2.41-2.31 (m, 1H); 2.15-2.06 (m, 1H); 1.92-1.83 (m, 1H); 1.66 (ddd, J=14.0, 9.7, 4.9 Hz, 1H). HRMS m/z (M+H) 253.1093 found, 253.1095 required. 1H NMR (1-10) (500 MHz, DMSO): δ 8.95 (s, 1H); 8.14 (s, 2H); 8.06 (d, J=4.5 Hz, 1H); 4.96 (q, J=8.4 Hz, 1H); 4.10 (dd, J=8.7, 4.8 Hz, 1H); 4.02 (d, J=4.4 Hz, 1H); 2.38-2.29 (m, 1H); 2.20-2.11 (m, 2H); 1.72-1.65 (m, 1H). HRMS m/z (M+H) 253.1095 found, 253.1095 required.

Provenance & Evidence