Hydrogen Bromide → 1353151-22-0

HRID 1528279Notes

Reaction equation

HRID 1528279 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 mixed with acetone (40 mL, 10V) and the resulting suspension was heated to reflux and stirred for 0.5 h. To the mixture was then added HBr (48% aq., 0.9 mL, 7.78 mmol, 1.03 eq) in one portion and stirring was continued at reflux temperature for 0.5 h. The mixture was then allowed to cool to room temperature by removal of the heating source, and was stirred at room temperature for 6 h. The flask containing the mixture was then transferred to a refrigerator where it was kept for about 3 days at 2° C. to about 8° C. (in a closed vessel). The mixture was then filtered and the isolated solid was dried in a vacuum oven (35 mmHg) at 70° C. for 24 h to afford Nilotinib HBr form XI as a yellow solid. The sample was analyzed in ARL X-ray powder diffractometer model X'TRA-019, and 13C NMR spectra are provided in FIGS. 73-74.

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureto reflux
  3. temperatureat reflux temperature for 0.5 h
  4. stirringwas stirred at room temperature for 6 h
  5. additionThe flask containing the mixture
  6. waitwas kept for about 3 days at 2° C. to about 8° C.
  7. filtrationThe mixture was then filtered
  8. customthe isolated solid was dried in a vacuum oven (35 mmHg) at 70° C. for 24 h

Sources & evidence

ORD record
ord-dfb8020f8385463eb3a9c4b7c1d963ba
Source dataset
uspto-grants-2015_07
Patent number
US09090598B2

Reaction notes

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