4-(2-(Pyrrolidin-1-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine → HCID 178511900, compound

Participants

Reaction Steps

Methyl thiophene-2-carbimidothioate hydroiodide (1.239 g, 4.34 mmol) was added to a mixture of 4-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine (0.572 g, 2.172 mmol) in EtOH (20 mL). The reaction was stirred overnight at room temperature. The reaction was quenched with saturated sodium bicarbonate solution (30 mL). The mixture was then extracted with CH2Cl2 (50 mL), and 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 then 5% (2M NH3 MeOH)/CH2Cl2). The collected fractions gave compound 11 as light brown viscous liquid (0.71 g, 88%). 1H NMR (DMSO-d6) δ 7.69 (d, J=3.6 Hz, 1H), 7.56 (d, J=5.1 Hz, 1H), 7.08-7.06 (m, 1H), 6.67 (t, J=8.7 Hz, 1H), 6.50 (d, J=8.4 Hz, 1H), 6.46 (s, 1H), 6.32 (brs, 2H), 3.57-3.53 (m, 2H), 3.39-3.34 (m, 2H), 3.03-3.00 (m, 2H), 2.60 (t, J=7.2 Hz, 2H), 2.50 (brs, 4H), 1.68 (brs, 4H); ESI-MS (m/z, %): 375, 373 (MH+, 47), 278, 276 (100), 98 (21).

Provenance & Evidence