Water → HCID 21866466, compound

Temperature

22.5 °C

75.0 g (0.29 mol) of BOC-protected thiazolecarboxamide (VI) were suspended in 524 ml of dichloromethane and, at from −5° to 0° C., admixed with 78.9 g (0.78 mol) of triethylamine and 79.5 g (0.38 mol) of trifluoroacetic anhydride. The mixture was stirred for one hour and allowed to warm to 20-25° C., 1190 ml of water were added and the phases were separated. 160 ml of 5-6 N isopropanolic HCl were added to the organic phase, the mixture was heated to the boil for 3 h, stirred at 20-25° C. overnight and cooled to from −5 to 0° C. for 2.5 h, and the solid was filtered off. It was washed with dichloromethane and dried. This gave 48.1 g of 2-aminomethyl-4-cyanothiazole of a purity by HPLC of 99.4 area %, which corresponds to a yield of 94.3% for these two steps.

1. customthe phases were separated
2. addition160 ml of 5-6 N isopropanolic HCl were added to the organic phase
3. temperaturethe mixture was heated to the boil for 3 h
4. stirringstirred at 20-25° C. overnight
5. temperaturecooled to from −5 to 0° C. for 2.5 h
6. filtrationthe solid was filtered off
7. washIt was washed with dichloromethane
8. customdried

ORD record

ord-2f472c09b8a74927a9d61a9d2ef05205

Source dataset

uspto-grants-2003_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06639081B1