2,3-Dihydroxybutanedioic Acid → L-Tartaric acid

A saturated solution of l-tartaric acid was prepared at 25 C by dissolving tartaric acid in a 85/15 v/v THF/water mixture. This solution (2 mL) was heated 2 to 65 C. Approximately 200 mg of N-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea free base solid was then added, which readily dissolved. N-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea L-bitartrate crystallized within 30 minutes from this clear solution. The slurry was then diluted with the saturated solution (at 25° C.) of l-tartaric acid and cooled to ambient temperatures. The slurry was continue to be stirred overnight and the solids were isolated via filtration. The filtered solids were washed with 85/15 v/v mixture of THF/water to remove excess l-tartaric acid and then dried in the oven at 45° C.

1. dissolutionwhich readily dissolved
2. customN-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea L-bitartrate crystallized within 30 minutes from this clear solution
3. additionThe slurry was then diluted with the saturated solution (at 25° C.) of l-tartaric acid
4. temperaturecooled to ambient temperatures
5. customthe solids were isolated via filtration
6. washThe filtered solids were washed with 85/15 v/v mixture of THF/water
7. customto remove excess l-tartaric acid
8. customdried in the oven at 45° C.

ORD record

ord-778fb59ef0a3477da7892785237e6397

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633317B2