Triethylamine → (4R)-3-Fluoro-4-({4-[([1,2,3]thiadiazolo[5,4-b]pyridin-6-ylmethyl)amino]-1-piperidinyl}methyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Dihydrochloride

Participants

Reaction Steps

To a solution of [1,2,3]thiadiazolo[5,4-b]pyridin-6-ylmethanol (for a synthesis see WO2003064431, Example 1(b(iv)) (28 mg, 0.166 mmol) in THF (1 ml) was added triethylamine (0.023 ml, 0.166 mmol) and then methanesulfonyl chloride (0.013 ml, 0.166 mmol) and the reaction was then stirred at room temperature for 2 h. DMF (1 ml) was then added followed by (4R)-4-[(4-amino-1-piperidinyl)methyl]-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Enantiomer 1 (50 mg, 0.166 mmol) and potassium carbonate (0.166 mmol) and the reaction was stirred at room temperature for a further 72 h before evaporation. The residue was subjected to column chromatography on silica gel using a dichloromethane, methanol gradient to provide the free base of the title compound (20 mg, 27%).

Provenance & Evidence