Hydrochloric Acid → HCID 71506752, compound

Participants

Reaction Steps

{(1S,2S,4R)-4-[(6-{[(1R,2S)-5-chloro-2-methoxy-2,3-dihydro-1H-inden-1-yl]amino}pyrimidin-4-yl)oxy]-2-hydroxycyclopentyl}methyl sulfamate 1-216 (4.44 g, 0.00916 mol) was placed in a 250-ml round bottomed flask equipped with a stir bar. Acetonitrile (82.5 mL) was added with stirring. The mixture was stirred and sonicated for several minutes (the solids did not fully dissolve). The flask was immersed in an ice bath and then, with stirring, aqueous hydrochloric acid (6.0M, 1.69 mL, 0.0101 mol) was added in a slow stream during which time the solids partially dissolved. The ice bath was removed and the reaction mixture was stirred at room temperature under an atmosphere of nitrogen for 2 hours during which time a dense white precipitate formed. Diethyl ether (82.5 mL) was added with stirring and the resulting mixture was stored in a refrigerator overnight. The precipitated product was collected on a fritted funnel, washed with cold ether, then dried for 24 hours at 42° C. under high vacuum to afford the title compound as a fluffy white powder, 3.84 g (80% yield). LCMS: formic acid, [M+H+]=485.2. 1H NMR (400 MHz, MeOD) δ 8.42 (s, 1H), 7.30 (s, 1H), 7.27-7.18 (m, 2H), 6.26 (s, 1H), 5.78 (s, 1H), 5.30 (s, 1H), 4.46-4.38 (td, J=5.2, 2.0 Hz, 1H), 4.39-4.25 (m, 2H), 4.23-4.13 (dd, J=9.9, 7.4 Hz, 1H), 3.37 (s, 3H), 3.18-3.04 (m, 2H), 2.62-2.47 (m, 1H), 2.42-2.31 (ddd, J=15.0, 6.9, 2.0 Hz, 1H), 2.24-2.14 (dt, J=15.0, 4.6 Hz, 1H), 2.14-2.02 (dd, J=10.3, 5.9 Hz, 2H).

Provenance & Evidence