Hydrochloric Acid → HCID 136348415, compound

Participants

Reaction Steps

A mixture of methyl 3-chloro-4-[1-methyl-3-(2-pyridyl)-4,6,7,8-tetrahydropyrazolo[3,4-e][1,4]thiazepin-4-yl]benzoate (0.060 g, 0.15 mmol, Example #E.1), methanol (5 mL), THF (5 mL) and 2 M aqueous NaOH (3 mL) was stirred at rt for about 18 h. Subsequently, 1 M aqueous HCl (7 mL) was added and the volatiles were removed in vacuo. The residue was treated with water (20 mL) and then extracted with ethyl acetate (2×70 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by prep-HPLC (Table 2, Method a) to give 3-chloro-4-[1-methyl-3-(2-pyridyl)-4,6,7,8-tetrahydropyrazolo[3,4-e][1,4]thiazepin-4-yl]benzoic acid (0.016 g, 0.04 mmol, 27%) as an off white solid: LC-MS (Table 1, Method a) Rt=3.0 min; m/z 401 (M+H)+; 1H-NMR (CDCl3, Bruker 400 MHz) δ 2.58-2.75 (2H, m) 3.06 (1H, t, J=11.8 Hz) 3.68-3.76 (1H, m) 3.77 (3H, s) 5.82 (1H, d) 7.03 (1H, s) 7.14-7.18 (1H, m) 7.42 (1H, d, J=8.0 Hz) 7.66-7.72 (2H, m) 7.79 (1H, d, J=8.0 Hz) 7.89 (1H, d, J=1.7 Hz) 8.43-8.48 (1H, m).

Provenance & Evidence