Methanol → HCID 68992268, compound

Participants

Reaction Steps

(6-fluoro-2-oxo[1,3]thiazolo[5,4-b]pyridin-1(2H)-yl)acetaldehyde (0.046 g, 0.22 mmole) and 1,1-dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-4-piperidinylcarbamate (0.069 g, 0.2 mmole) (for a synthesis see WO2004/058144 Example 99(h)) were dissolved in chloroform (5 ml) and MeOH (1 ml) and treated with acetic acid (10 drops) and (polystyrylmethyl)trimethylammonium cyanoborohydride (Novabiochem) (4.1 mmol/g, 0.39 g), and the mixture stirred at rt for 60 h. The reaction was filtered and evaporated to dryness to give 1,1-dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl) {1-[2-(6-fluoro-2-oxo[1,3]thiazolo[5,4-b]pyridin-1(2H)-yl)ethyl]-4-piperidinyl}. This was dissolved in DCM (3 ml) and treated with trifluoroacetic acid (1 ml) at rt for 4 h then evaporated to dryness. The residue was dissolved in MeOH, stirred with polymer supported carbonate resin and then filtered and evaporated. Chromatography on silica gel of the residue, eluting with a gradient of 0-12% 2M ammonia in MeOH/DCM gave the free base of the title compound (0.05 g, 51%)

Provenance & Evidence