Hydrogen Bromide → 1353151-22-0

HRID 1528283Notes

Reaction equation

HRID 1528283 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]>CC(C)=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 180AcetoneSolvent

Procedure

Nilotinib base Form A (4.00 g, 7.55 mmol) was suspended in acetone (40 mL). The resulting mixture was stirred and heated to reflux for 0.5 h. HBr (48% aq., 0.88 mL, 7.78 mmol, 1.03 eq) was then added in one portion. The resulting mixture was refluxed for 10 min and then cooled to room temperature over 1 h. Then it was stirred at room temperature over 16 h and a solid precipitate formed. The solid was isolated by vacuum filtration and dried in a vacuum oven at 70° C. for 32 h to give Nilotinib HBr form XI as a yellow solid (4.42 g, 96%). Monohydrobromide salt was obtained according to assay determination.

Workup

  1. temperatureheated
  2. temperatureto reflux for 0.5 h
  3. temperatureThe resulting mixture was refluxed for 10 min
  4. stirringThen it was stirred at room temperature over 16 h
  5. customa solid precipitate formed
  6. customThe solid was isolated by vacuum filtration
  7. customdried in a vacuum oven at 70° C. for 32 h

Sources & evidence

ORD record
ord-e85ebf0c863c44acbf5e03209ded3989
Source dataset
uspto-grants-2015_07
Patent number
US09090598B2

Reaction notes

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