Hydrochloric Acid → HCID 178484223, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of tert-butyl methyl(2-(6-(thiophene-2-carboximidamido)-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)carbamate (415 mg, 0.959 mmol) in methanol (4 mL) was added a 3N HCl solution (3.198 mL, 9.59 mmol). The resulting mixture was then stirred at 90° C. for 1 hour. The mixture was then cooled to room temperature, diluted with water, basified with 3N sodium hydroxide to pH 12, and extracted with dichloromethane (3×). The combined organics were dried, filtered, and concentrated then chromatographed in 1:9 (2M NH3 in methanol):ethyl acetate, giving the desired product 28 (165 mg, 51.7%). 1H NMR (DMSO-d6) δ 7.71 (d, J=3.0 Hz, 1H), 7.58 (d, J=5.1 Hz, 1H), 7.10-7.06 (m, 1H), 6.82 (d, J=8.1 Hz, 1H), 6.34 (brs, 2H), 6.22 (s, 1H), 6.07 (d, J=8.1 Hz, 1H), 3.62-3.57 (m, 2H), 3.32 (t, J=6.8 Hz, 2H), 3.01-2.97 (m, 2H), 2.64 (t, J=6.8 Hz, 1H), 2.29 (s, 3H). ESI-MS (m/z, %): 333 (MH+, 100), 276 (71); ESI-HRMS calculated for C16H21N4S2 (MH+), calculated: 333.1202, observed: 333.1207; HPLC purity: 97% by area.

Provenance & Evidence