Ethanol → HCID 71203610, compound

Temperature

92.5 °C

Piperidine (1.84 g, 21.63 mmol) was added to a stirred solution of ethyl 5-(4-methoxyphenyl)-4-methylthiazole-2-carboxylate (prepared according to the procedure reported in WO 2006/089076, 0.6 g, 2.16 mmol) in a ethanol (10 ml) in a tube at 25° C. under nitrogen atmosphere. The tube was agitated for about 15 minutes under nitrogen and was sealed. The reaction mixture was heated at 90-95° C. for 15 hr with stirring. The progress of the reaction was monitored by TLC. The reaction mixture was then cooled to 25° C. and was concentrated under reduced pressure. The residue obtained was dissolved in ethyl acetate (50 ml). The mixture was washed with saturated sodium bicarbonate solution (20 ml). The separated organic layer was concentrated under reduced pressure to obtain a crude product, which was then purified by flash column chromatography using 40% ethyl acetate in hexanes as an eluent to obtain the title compound (0.50 g, 73.0%).

1. customprepared
2. customat 25° C.
3. customwas sealed
4. stirringwith stirring
5. temperatureThe reaction mixture was then cooled to 25° C.
6. concentrationwas concentrated under reduced pressure
7. customThe residue obtained
8. washThe mixture was washed with saturated sodium bicarbonate solution (20 ml)
9. concentrationThe separated organic layer was concentrated under reduced pressure
10. customto obtain a crude product, which
11. customwas then purified by flash column chromatography

ORD record

ord-fc6c47b3856f4a14aeba67c6f8eac176

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946432B2