HCID 59144174, compound → HCID 178464032, compound

Participants

Reaction Steps

Methyl thiophene-2-carbimidothioate hydroiodide (2.266 g, 7.94 mmol) was added to a mixture of 4-(2-(diethylamino)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine (1.054 g, 3.97 mmol) in EtOH (20 mL). The mixture was stirred for 2 days at room temperature. The reaction was quenched with saturated sodium bicarbonate solution (30 mL) and extracted with CH2Cl2 (50 mL). The aqueous phase was washed with CH2Cl2 (50 mL). The combined organic fractions were washed with brine (50 mL) and dried (Na2SO4). The crude material was subject to flash chromatography on silica gel (CH2Cl2 followed by 3.5% (2M NH3 in MeOH):CH2Cl2). The collected fractions were concentrated, and the sample was subjected again to flash chromatography on silica gel (2.5% MeOH:CH2Cl2). The collected fractions were concentrated to give compound 15 as a brown solid. (1.23 g, 83%). 1H NMR (CDCl3) δ 7.40-7.36 (m, 2H), 7.05 (dd, J=3.9, 4.8 Hz, 1H), 6.73 (m, 3H), 3.65-3.61 (m, 1H), 3.39 (t, J=7.2 Hz, 2H), 3.05-3.02 (m, 2H), 2.67-2.54 (m, 6H), 1.04 (t, J=7.2 Hz, 6H); ESI-MS (m/z, %): 377, 375 (MH+, 35), 278, 276 (100).

Provenance & Evidence