反应详情

温度

-10 °C

1-(2,2-Dimethylpropyl)-5-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (31-4, 53.2 mg, 0.18 mmol, 1.0 equiv) was added to anhydrous DCM (1.8 mL) and cooled to −10° C. Triethylamine (108 μL, 0.77 mmol, 4.2 equiv) and methanesulfonyl chloride (32 μL, 0.40 mmol, 2.2 equiv) were added sequentially and the resulting reaction mixture was stirred for 1 min. Following this duration, TLC showed complete consumption of 31-4. The reaction mixture was partitioned between ethyl acetate (5 mL) and saturated NaHCO3 (5 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (3×5 mL). The combined organics were dried over Na2SO4, filtered and concentrated in vacuo to give a clear, yellow oil. The crude product was carried forward without further purification.

1. customthe resulting reaction mixture
2. customconsumption of 31-4
3. customThe reaction mixture was partitioned between ethyl acetate (5 mL) and saturated NaHCO3 (5 mL)
4. customThe layers were separated
5. extractionthe aqueous layer was extracted with ethyl acetate (3×5 mL)
6. dry with materialThe combined organics were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto give a clear, yellow oil
10. customThe crude product was carried forward without further purification