Hydrogen Bromide → 1353151-22-0

HRID 1428318Notes

Reaction equation

HRID 1428318 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.CN(C)C=O.[BrH:45]>CCO>[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:45]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 6228DimethylformamideHCID 644241Nilotinib

Product 1

HCID 565926751353151-22-0

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Nilotinib base Form A (4.00 g, 7.55 mmol) was suspended in EtOH abs. (40 mL, 10V) at room temperature. The suspension was heated to 80° C. and stirred for 30 min. HBr (48% aq., 0.9 mL, 7.78 mmol, 1.03 eq) was added in one portion. The suspension was stirred for one hour at 80° C. then cooled to ambient temperature by removal of the heating source. The stirring was then continued for about 20 h. A yellow solid was isolated by filtering the suspension thereby providing Nilotinib HBr form VIII. The sample was analyzed by PXRD (ARL X-ray powder diffractometer model X'TRA-019).

Workup

  1. customat room temperature
  2. stirringThe suspension was stirred for one hour at 80° C.
  3. temperaturethen cooled to ambient temperature by removal of the heating source
  4. waitThe stirring was then continued for about 20 h
  5. customA yellow solid was isolated
  6. filtrationby filtering the suspension

Sources & evidence

ORD record
ord-1fd6d6adc95642b5af4a573c563bcf25
Source dataset
uspto-grants-2015_01
Patent number
US08937082B2

Reaction notes

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