Hydrogen Bromide → HCID 178517614, compound

Participants

Reaction Steps

A solution of (R)-6-(2-methoxypyrimidin-5-yl)-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazole (Example 15, 20 mg, 0.051 mmol) in hydrobromic acid (48 wt. % in water, 0.25 mL, 2.2 mmol) was heated to 80° C. for 1 hour, concentrated with a stream of nitrogen and chromatographed on silica gel eluting with 2 to 20% (9:1 methanol:ammonium hydroxide) in CH2Cl2 to provide the desired product. 1H NMR (300 MHz, CD3OD) δ ppm 1.48-1.57 (m, 2H), 1.62-1.72 (m, 4H), 1.98-2.10 (m, 1H), 2.32-2.43 (m, 1H), 2.47-2.67 (m, 4H), 3.05-3.19 (m, 1H), 3.39-3.46 (m, 1H), 3.52-3.62 (m, 1H), 3.71-3.80 (m, 1H), 3.84-3.92 (m, 1H), 7.49 (dd, J=8.5, 1.7 Hz, 1H), 7.55 (d, J=8.5 Hz, 1H), 7.90 (d, J=1.4 Hz, 1H), 8.59 (s, 2H); MS (DCI/NH3) m/z 382 (M+H)+.

Provenance & Evidence