Pyridine → 6-methylimidazo[2,1-b][1,3]thiazole-5-carbonitrile

To a mixture of 6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide (544 mg, 3.0 mmol) produced above, pyridine (0.7 mL, 9.0 mmol) and tetrahydrofuran (10 mL) was added dropwise under ice-cooling trifluoroacetic anhydride (0.6 mL, 4.5 mmol). After stirring at room temperature for 1 day, saturated aqueous sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The collected organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→50/50). The obtained solution was concentrated under reduced pressure to give the title compound (433 mg, 86%) as a pale-brown solid.

1. additionwas added dropwise under ice-
2. extractionthe mixture was extracted with ethyl acetate
3. washThe collected organic layer was washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationthe insoluble material was filtered off
6. concentrationThe filtrate was concentrated under reduced pressure
7. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→50/50)
8. concentrationThe obtained solution was concentrated under reduced pressure

ORD record

ord-b0f3534717274fd18cfcd9e04eaf130e

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139589B2