Hydrogen Bromide → 1353151-22-0

HRID 1428310Notes

Reaction equation

HRID 1428310 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([NH:23][C:24]2[CH:25]=[C:26]([C:36]([F:39])([F:38])[F:37])[CH:27]=[C:28]([N:30]3[CH:34]=[N:33][C:32]([CH3:35])=[CH:31]3)[CH:29]=2)=[O:22])=[CH:6][C:7]=1[NH:8][C:9]1[N:10]=[CH:11][CH:12]=[C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[N:19][CH:20]=2)[N:14]=1.[BrH:40]>CN1CCCC1=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([NH:23][C:24]2[CH:25]=[C:26]([C:36]([F:38])([F:39])[F:37])[CH:27]=[C:28]([N:30]3[CH:34]=[N:33][C:32]([CH3:35])=[CH:31]3)[CH:29]=2)=[O:22])=[CH:6][C:7]=1[NH:8][C:9]1[N:10]=[CH:11][CH:12]=[C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[N:19][CH:20]=2)[N:14]=1.[BrH:40]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 644241Nilotinib

Product 1

HCID 565926751353151-22-0

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of Nilotinib base (2.00 g, 3.77 mmol) and TFE (12 mL, 6V) was stirred and heated to 55° C. to provide a clear pale yellow solution. The solution was cooled to 50° C. and HBr (48% aq, 0.4 mL, 8.31 mmol, 2.2 eq) was added. The resulting deep yellow solution was stirred at 50° C. for 1 h, and then cooled to ambient temperature. Stirring was continued for 2 h and then the mixture was cooled to 5° C. in an ice-bath. About ⅔V of the solvent were removed under reduced pressure and the resulting mixture was kept in a refrigerator (5° C.) overnight. A solid precipitated and was separated by filtration to give Nilotinib HBr form III.

Workup

  1. customto provide a clear pale yellow solution
  2. temperatureThe solution was cooled to 50° C.
  3. stirringThe resulting deep yellow solution was stirred at 50° C. for 1 h
  4. temperaturecooled to ambient temperature
  5. stirringStirring
  6. temperaturethe mixture was cooled to 5° C. in an ice-bath
  7. customAbout ⅔V of the solvent were removed under reduced pressure
  8. customwas kept in a refrigerator (5° C.) overnight
  9. customA solid precipitated
  10. customwas separated by filtration

Sources & evidence

ORD record
ord-7e132a4ea6054ca8a8b9389126c30e14
Source dataset
uspto-grants-2015_01
Patent number
US08937082B2

Reaction notes

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