Potassium Carbonate → HCID 178461159, compound

Participants

Reaction Conditions

Reaction Steps

To a solution containing 55 mg (0.15 mmol) of (5R,7S)-4-{[(1R,2R)-2-fluorocyclohexyl]amino}-1-(3-fluorophenyl)-7-methyl-1,3,8-triazaspiro[4.5]dec-3-en-2-one and (5R,7S)-4-{[(1S,2S)-2-fluorocyclohexyl]amino}-1-(3-fluorophenyl)-7-methyl-1,3,8-triazaspiro[4.5]dec-3-en-2-one in DMF (1.5 mL) was added powdered K2CO3 (81 mg, 0.58 mmol) and bromomethylcyclobutane (22 mg (0.15 mmol). The solution was heated to 60° C. overnight. The reaction was diluted with water (1.5 mL) and extracted three times with EtOAc. The combined organics were dried over MgSO4, filtered and concentrated then chromatographed using 100% EtOAc to give the desired product which was further purified on a Waters automated system affixed with a Chiralpak AD 5 cm×50 cm cartridge eluting at 80 mL/min with isocratic 20% ethyl alcohol in hexanes with no modifier. The second peak was the product. The salt could be formed as described for the examples in Table 5.

Provenance & Evidence