Hydrochloric Acid → HCID 178464394, compound

Participants

Reaction Steps

A solution of tert-butyl ethyl(2-(7-(thiophene-2-carboximidamido)-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)carbamate (0.4 g, 0.896 mmol) in methanol (10 mL) was treated with 3 N HCl (3.88 mL, 11.64 mmol) and stirred at reflux for 1.5 hours. The mixture was cooled to room temperature, diluted with water (20 mL), and basified with 1N NaOH. The product was extracted into dichloromethane (2×25 mL). The combined organic layer was dried (Na2SO4) and concentrated. The crude material was subjected to column chromatography on silica gel (5:95 (2M NH3 in MeOH):CH2Cl2) to give a yellow solid (0.142 g, 45.8%). 1H-NMR (DMSO-d6) δ 7.69 (dd, J=0.9, 3.6 Hz, 1H), 7.56 (d, J=5.1 Hz, 1H), 7.07 (dd, J=3.6, 4.8 Hz, 1H), 6.72 (d, J=8.7 Hz, 1H), 6.49 (dd, J=2.1, 8.4 Hz, 1H), 6.45 (d, J=2.1 Hz, 1H), 6.31 (brs, 2H), 3.55-3.51 (m, 2H), 3.30-3.24 (m, 2H), 3.04-3.00 (m, 2H), 2.62 (t, J=6.9 Hz, 2H), 2.56 (q, J=7.2 Hz, 2H), 1.01 (t, J=7.2 Hz, 3H); ESI-MS (m/z, %): 347 (MH+, 75%), 276 (100%); HPLC purity: 99.5% by area.

Provenance & Evidence