Hydrogen Bromide → HCID 178515839, compound

Participants

Reaction Steps

A solution of (R)-6-(6-methoxypyridazin-3-yl)-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazole (Example 68, 19.8 mg, 0.032 mmol) in hydrobromic acid (48 wt. % in water, 0.25 mL, 2.210 mmol) was heated to 80° C. for 1 hour, concentrated with a stream of nitrogen and chromatographed on silica gel eluting with a gradient of 2 to 10% (9:1 methanol:ammonium hydroxide) in CH2Cl2 to provide the desired product, (R)-6-(2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazol-6-yl)pyridazin-3-ol. 1H NMR (300 MHz, CD3OD) δ ppm 1.47-1.57 (m, 2H), 1.61-1.72 (m, 4H), 1.95-2.10 (m, 1H), 2.32-2.43 (m, 1H), 2.46-2.66 (m, 4H), 3.05-3.18 (m, 1H), 3.38-3.47 (m, 1H), 3.52-3.63 (m, 1H), 3.72-3.81 (m, 1H), 3.84-3.92 (m, 1H), 7.05 (d, J=9.8 Hz, 1H), 7.54 (d, J=8.5 Hz, 1H), 7.83 (dd, J=8.5, 2.0 Hz, 1H), 8.06 (d, J=9.8 Hz, 1H), 8.21 (d, J=1.7 Hz, 1H); MS (DCI/NH3) m/z 382 (M+H)+.

Provenance & Evidence