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0 °C

To a solution of 1-{(2R)-2-(cyclopentylmethyl)-4-[(1,1-dimethylethyl)oxy]-4-oxobutanoyl}-4,5-dihydro-1H-pyrazole-5-carboxylic acid (352 mg, 1.0 mmol) in acetonitrile (10 mL) at 0° C. was added 4-[4,6-bis(methyloxy)-1,3,5-triazin-2-yl]-4-methylmorpholin-4-ium (656 mg, 2.0 mmol) and N-methylmorpholine (0.29 mL, 2.6 mmol). The reaction was stirred for 2 hours at 0° C., and then 6-(1-methylethyl)-2-pyridinamine (177 mg, 1.30 mmol) was added to the reaction. The mixture was allowed to warm to room temperature and was stirred for 3 hours. The solvent was removed under reduced pressure, and then water (5 mL) and DCM (15 mL) were added. The phases were separated. The aqueous phase was extracted twice with DCM (15 mL), and the combined organics were dried over sodium sulfate and concentrated. The resulting residue was purified by Combiflash silica gel chromatography (0-100% EtOAc in hex) to give 1,1-dimethylethyl (3R)-3-(cyclopentylmethyl)-4-(5-{[(6-ethyl-2-pyridinyl)amino]carbonyl}-4,5-dihydro-1H-pyrazol-1-yl)-4-oxobutanoate (368 mg, 0.81 mmol, 81% yield) as a yellow oil. MS: 457 ([M+H]+).

1. temperatureto warm to room temperature
2. stirringwas stirred for 3 hours
3. customThe solvent was removed under reduced pressure
4. additionwater (5 mL) and DCM (15 mL) were added
5. customThe phases were separated
6. extractionThe aqueous phase was extracted twice with DCM (15 mL)
7. dry with materialthe combined organics were dried over sodium sulfate
8. concentrationconcentrated
9. customThe resulting residue was purified by Combiflash silica gel chromatography (0-100% EtOAc in hex)