tert-Butyl 2-(7-amino-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl(methyl)carbamate → HCID 178484228, compound

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Reaction Steps

Benzyl furan-2-carbimidothioate hydrobromide (1.199 g, 4.02 mmol) was added to a mixture of tert-butyl 2-(7-amino-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl(methyl)carbamate (0.763 g, 2.361 mmol) in EtOH (20 mL). The mixture was stirred under room temperature overnight. The mixture was quenched with saturated sodium bicarbonate solution (50 mL), diluted with water (50 mL), and extracted with CH2Cl2 (2×50 mL). The organic phase was washed with brine (50 mL) and dried (Na2SO4). The crude material was subject to flash chromatography on silica gel (2.5-5% (2M NH3 in MeOH):CH2Cl2). The collected fractions were concentrated to give a white foam (0.88 g, 90%). 1H NMR (CDCl3) δ 7.85 (s, 1H), 7.44 (s, 1H), 6.74-6.69 (m, 1H), 6.62 (d, J=7.5 Hz, 1H), 4.72 (brs, 2H), 3.64-3.60 (m, 2H), 3.41 (s, 4H), 3.04-3.01 (m, 2H), 2.92 (s, 3H), 1.45 (s, 9H); ESI-MS (m/z, %): 419, 417 (MH+, 100).

Provenance & Evidence