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Benzyl furan-2-carbimidothioate hydrobromide (1.139 g, 3.82 mmol) was added to a mixture of 4-(2-(dimethylamino)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine (0.829 g, 3.49 mmol) in EtOH (20 mL). The mixture was stirred for 2 days under argon atmosphere. The solution was quenched with saturated sodium bicarbonate (50 mL). The solution was transferred to a separatory funnel, diluted with water (50 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 subjected to flash chromatography on silica gel (2.5-5% (2M NH3 in MeOH):CH2Cl2). The collected fractions gave compound 19 as a brown oil (1.03 g, 90%). 1H NMR (CDCl3) δ 7.46 (s, 1H), 7.03 (brs, 1H), 6.73-6.68 (m, 3H), 6.50 (brs, 1H), 5.03 (brs, 2H), 3.62-3.59 (m, 2H), 3.40 (t, J=7.2 Hz, 2H), 3.05-3.02 (m, 2H), 2.52 (t, J=7.5 Hz, 2H), 2.29 (s, 6H); ESI-MS (m/z, %): 333, 331 (MH+, 91), 260, 262 (100).

1. customThe solution was quenched with saturated sodium bicarbonate (50 mL)
2. customThe solution was transferred to a separatory funnel
3. additiondiluted with water (50 mL)
4. extractionextracted with CH2Cl2 (50 mL)
5. washThe aqueous phase was washed with CH2Cl2 (50 mL)
6. washThe combined organic fractions were washed with brine (50 mL)
7. dry with materialdried (Na2SO4)