Pyridine → 2-isobutyramido-N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)isonicotinamide

To a mixture of 2-amino-N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)isonicotinamide (25 mg, 0.073 mmol, Step-1, single enantiomer) and pyridine (0.024 mL, 0.29 mmol) in N,N-dimethylacetamide (1 mL) is added isobutyryl chloride (16 mg, 0.15 mmol) at room temperature. After stirring at room temperature for 2 hours, the mixture is poured onto water (2 mL), and the mixture is extracted with ethyl acetate (3 mL). The organic layer is dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography on NH-silica gel eluting with ethyl acetate and then by preparative LC-MS to give 12.9 mg (43% yield) of the title compound.

1. additionthe mixture is poured onto water (2 mL)
2. extractionthe mixture is extracted with ethyl acetate (3 mL)
3. dry with materialThe organic layer is dried over sodium sulfate
4. concentrationconcentrated under reduced pressure
5. customThe residue is purified by column chromatography on NH-silica gel eluting with ethyl acetate

ORD record

ord-40c8ab920f684f64925159b04c3fb71e

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09302991B2