Triethylamine → 4-[(4-{[(3-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methyl]amino}-1-piperidinyl)methyl]-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Dihydrochloride

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To a solution of the dihydrochloride salt of 4-[(4-amino-1-piperidinyl)methyl]-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one (56 mg, 0.158 mmol) in methanol (0.4 ml), dichloromethane (1.6 ml) was added triethylamine (110 μl, 0.79 mmol) and 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxaldehyde (for a synthesis see WO2003087098, Example 301(d)) (31 mg, 0.158 mmol). This mixture was stirred for 18 h at 25° C. before NaBH4 (6 mg, 0.158 mmol) was added and the reaction stirred for a further 0.5 h after which time the solvent was evaporated and the residue was subjected to column chromatography on silica gel using a 0-30% methanol in dichloromethane gradient. This provided the free base of the title compound as a yellow solid (30 mg, 41%).

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