Phosphorus oxychloride → HCID 86711220, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of dimethylacroleine (0.250 ml, 2.52 mmol) and POCl3 (0.235 ml, 2.52 mmol) in dichloroethane (2 ml) at 0° C. for 15 min was added N,N-diisopentyl-2-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridine-5-carboxamide (0.26 g, 0.630 mmol). The mixture was heated to 65° C. for 6 h. Mixed more reagents for 15 min then added to solution above and stirred at 65° C. for 12 h. Water (20 ml) was added to the cooled mixture and extracted with DCM (3×25 ml). The combined organics (liquids and solids) were concentrated to afford a red semisolid. The residue was treated with saturated sodium bicarbonate (20 ml) and MeOH (20 ml) overnight. The suspension was neutralized with a saturated NH4Cl solution and extracted with DCM (3×100 ml). The combined organics were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography: ISCO 24 g eluting with 0% to 100% ethyl acetate in hexanes over 12 min. Pooled and concentrated desired fractions to afford, 0.23 g (78%) of the title compound as a yellow oil. LCMS m/z 469.3 (M+H)+. ret. time=2.29 min

Provenance & Evidence