Dimethylamine → N-(7-dimethylaminomethyl-1-methyl-2,2-dioxo-1,2,3,4-tetrahydro-2lambda6-benzo[c][1,2]thiazin-4-yl)-3-(naphthalen-2-yl-sulfonylamino)-3-phenyl-propionamide

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Reaction Steps

Methanesulfonic anhydride (100 mg, 0.55 mmol) was added to a THF (5 mL) solution of N-(7-hydroxymethyl-1-methyl-2,2-dioxo-1,2,3,4-tetrahydro-2λ6-benzo[c][1,2]thiazin-4-yl)-3-(naphthalen-2-yl-sulfonylamino)-3-phenyl-propionamide (Step D) (200 mg, 0.345 mmol) and N-methylmorpholine (0.11 mL, 0.55 mmol). After 30 min stirring, Me2NH (1.73 mL, 3.45 mmol, 2.0 M in THF) was added to this freshly prepared mesylate solution. After stirring overnight, the mixture was diluted with CH2Cl2 (30 mL), washed with H2O, dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica (0-5% MeOH in CH2Cl2) provided the title compound. MS (+ESI, m/z): 607 (M+H)+.

Provenance & Evidence