反应详情

A solution of 2-chloro-5-(trifluoromethyl)pyrazine (CAS number 799557-87-2; 6.78 ml, 54.9 mmol), tert-butyl N-[(1S,2S)-2-aminocyclopentyl]carbamate (CAS number 586961-34-4; 10 g, 49.9 mmol) and DIPEA (26.2 ml, 150 mmol) in DMSO (160 ml) was heated at 140° C. for 18 hours. The reaction mixture was partitioned between ethyl acetate (200 ml) and water (200 ml). The aqueous layer was extracted with ethyl acetate (2×100 ml). The combined organics were washed with brine (3×100 ml), filtered through a hydrophobic frit, further dried over magnesium sulphate and then concentrated in vacuo. The resulting residue was purified by column chromatography (silica, 0-40% ethyl acetate/petrol). Impure fractions were further purified by column chromatography (silica, 10-40% ethyl acetate/petrol) and combined to afford the title compound.

1. customThe reaction mixture was partitioned between ethyl acetate (200 ml) and water (200 ml)
2. extractionThe aqueous layer was extracted with ethyl acetate (2×100 ml)
3. washThe combined organics were washed with brine (3×100 ml)
4. filtrationfiltered through a hydrophobic frit
5. dry with materialfurther dried over magnesium sulphate
6. concentrationconcentrated in vacuo
7. customThe resulting residue was purified by column chromatography (silica, 0-40% ethyl acetate/petrol)
8. customImpure fractions were further purified by column chromatography (silica, 10-40% ethyl acetate/petrol)