Hydrochloric Acid → HCID 178478761, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 2-hydroxyethyl(2-(7-(thiophene-2-carboximidamido)-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)carbamate (130 mg, 0.281 mmol) in MeOH (10 mL) was added 3N HCl (2.81 mL, 8.43 mmol). The yellow solution was heated at 75° C. for 30 minutes. At this time, the reaction was filtered and concentrated to half its volume. The yellow solution was then extracted with 2×50 mL CH2Cl2, and the aqueous layer was concentrated to dryness to give a yellow residue. This residue was dried under reduced (high vacuum) pressure to give compound 16 as yellow powder. 1H-NMR (CD3OD) δ 7.98-7.94 (m, 2H), 7.29 (pseudo t, J=4.2 Hz, 1H), 7.04-6.94 (m, 3H), 3.79 (brt, J=4.8 Hz, 2H), 3.72-3.65 (m, 4H), 3.28 (brs, 2H), 3.16 (brt, J=5.1 Hz, 2H), 3.09-3.06 (m, 2H); ESI-MS (m/z, %): 363 (MH+, free base, 100), 276 (90); ESI-HRMS calculated for C17H23N4O1S2 (MH+, free base): 363.1307, observed: 363.1316; HPLC purity: 96.2% a/a.

Provenance & Evidence