Water → HCID 178509227, compound

HRID 1677648Notes

Reaction equation

HRID 1677648 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:22]=3[O:31]C)=[O:19])=[CH:13][CH:12]=2)[NH:4][N:3]=1.B(Br)(Br)Br.O>ClCCl>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[C:11]2[CH:12]=[CH:13][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:24]=[CH:23][C:22]=3[OH:31])=[O:19])=[CH:15][CH:16]=2)[NH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 178490593HCID 178490593, compound

Product 1

HCID 178509227HCID 178509227, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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:

Workup

  1. customto return to 20° C
  2. temperaturethe reaction is cooled on an ice bath
  3. filtrationthe mixture is filtered off
  4. washthe insoluble orange material is washed with water and with dichloromethane
  5. customThe solid is purified on a prepacked Biotage KP-Sil column of 60 Å SiO2 32-63 μm (eluent

Sources & evidence

ORD record
ord-254fbc79d9e1416aaf78ae76c7875f88
Source dataset
uspto-grants-2011_08
Patent number
US08008322B2

Reaction notes

Loading…