Methanol → N-[5-(3-amino-4-chlorophenoxy) [1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide

Sodium borohydride (5.63 g, 149 mmol) was suspended in ethanol (100 mL), and methanol (66 mL) was gradually added. While cooling in a water bath, to the obtained reaction mixture was added N-(5-{4-chloro-3-[(trifluoroacetyl)amino]phenoxy}[1,3]thiazolo[5,4-b]pyridin-2-yl)cyclopropanecarboxamide (3.4 g, 7.44 mmol) powder by small portions, and thereafter the mixture was stirred at room temperature, for 1 hr. The reaction mixture was diluted with ethyl acetate (150 mL), and partitioned with water (200 ml). The organic layer was concentrated under reduced pressure. The residue was diluted with ethyl acetate (200 mL), and washed with saturated brine (100 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate/methanol=100/0), and triturated with diisopropyl ether to give the title compound (2.00 g, 75%) as a colorless powder.

1. temperatureWhile cooling in a water bath, to the obtained reaction mixture
2. custompartitioned with water (200 ml)
3. concentrationThe organic layer was concentrated under reduced pressure
4. additionThe residue was diluted with ethyl acetate (200 mL)
5. washwashed with saturated brine (100 mL)
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by basic silica gel column chromatography (ethyl acetate/methanol=100/0)
9. customtriturated with diisopropyl ether

ORDレコード

ord-35398e8ded0d4476b2735b21cb899481

出典データセット

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08697874B2