Hydrochloric Acid → HCID 178511894, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of tert-butyl 2-hydroxyethyl(2-(6-(thiophene-2-carboximidamido)-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)carbamate (334 mg, 0.722 mmol) in methanol (5 mL) was added HCl, 3M in water (2.407 mL, 7.22 mmol). The resulting solution was stirred at 90° C. for 1 hour. The mixture was then cooled to room temperature, diluted with saturated sodium carbonate and extracted with dichloromethane (6×). The combined organics were dried, filtered, concentrated, and then chromatographed in 1:9 (2M NH3 in methanol):ethyl acetate, giving the desired product 26 (175 mg, 66.9%). 1H NMR (DMSO-d6) δ 7.71 (d, J=3.3 Hz, 1H), 7.58 (d, J=5.1 Hz, 1H), 7.10-7.06 (m, 1H), 6.83 (d, J=8.1 Hz, 1H), 6.34 (brs, 2H), 6.22 (s, 1H), 6.07 (d, J=7.5 Hz, 1H), 4.49-4.43 (m, 1H), 3.63-3.55 (m, 2H), 3.46-3.38 (m, 2H), 3.37-3.28 (m, 2H), 3.01-2.95 (m, 2H), 2.71 (t, J=6.4 Hz, 2H), 2.59 (t, J=5.7 Hz, 2H), 1.91-1.75 (m, 1H); ESI-MS (m/z, %): 363 (MH+, 100), 276 (99), 268 (62); HRMS calculated for C17H23N4OS2 (MH+), calculated: 363.1307, observed: 363.1290; HPLC purity: 97% by area.

Provenance & Evidence