Water → HCID 178509227, compound

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Reaction Steps

To a solution of 1-[4-(3-amino-1H-pyrazolo[3,4-b]pyrid-4-yl)phenyl]-3-(2-methoxy-5-trifluoromethylphenyl)urea, described in Example 5, in 6 mL of dichloromethane at −40° C. are added dropwise 1.6 mL of 1M boron tribromide solution, and the temperature is allowed to return to 20° C. After 30 minutes, the reaction is cooled on an ice bath and water is then added. After stirring for 15 minutes, the mixture is filtered off and the insoluble orange material is washed with water and with dichloromethane. The solid is purified on a prepacked Biotage KP-Sil column of 60 Å SiO2 32-63 μm (eluent: 95/5 then 90/10 then 80/20 then 70/30 dichloromethane/solution A; solution A=38/17/2 dichloromethane/methanol/aqueous ammonia). 29 mg of a yellow powder of 1-[4-(3-Amino-1H-pyrazolo[3,4-b]pyrid-4-yl)phenyl]-3-(2-hydroxy-5-trifluoromethylphenyl)urea are obtained, the characteristics of which are as follows:

Provenance & Evidence