Hydrogen Bromide → 1353151-22-0

HRID 1428320Notes

Reaction equation

HRID 1428320 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]>CN(C)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 6228DimethylformamideSolvent

Procedure

Nilotinib base Form A (4.00 g, 7.55 mmol) was suspended in acetone (40 mL, 10V) at room temperature. The suspension was heated to reflux and stirred for 30 min. HBr (33% in acetic acid, 1.4 mL, 7.78 mmol, 1.03 eq) was added in one portion. The suspension was stirred for 1 h at reflux and then cooled to ambient temperature by removal of the heating source. The stirring was continued for about 6 h. The resulting yellow solid was isolated by filtration and dried in a vacuum oven (35 mmHg) at 70° C. for 15 h to give Nilotinib HBr form X as a yellow solid. (ARL X-ray powder diffractometer model X'TRA-019).

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux
  3. stirringThe suspension was stirred for 1 h
  4. temperatureat reflux
  5. waitThe stirring was continued for about 6 h
  6. customThe resulting yellow solid was isolated by filtration
  7. customdried in a vacuum oven (35 mmHg) at 70° C. for 15 h

Sources & evidence

ORD record
ord-b07a8768724c4ea4a6bd554016c55cb6
Source dataset
uspto-grants-2015_01
Patent number
US08937082B2

Reaction notes

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