Hydrogen Bromide → 1353151-22-0

HRID 1528270Notes

Reaction equation

HRID 1528270 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]>C(O)(=O)C>[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 176Acetic AcidSolvent3×

Conditions

Temperature
40 °C

Procedure

Nilotinib base (2.00 g, 3.77 mmol) was mixed with glacial acetic acid (8.00 mL, 4.0V). The mixture was heated to 40° C. with stirring which lead to a clear yellow solution. HBr 33% in acetic acid (0.8 mL, 4.53 mmol, 1.2 eq) was added in one portion to the stirred solution, leading to the formation of a yellow suspension. Stirring was continued at 40° C. over a period of 1 h. Due to the high viscosity of the mixture another 5 mL acetic acid (2.5V) was added. The mixture was then allowed to cool to room temperature by removal of the heat source, and the mixture was stirred at room temperature for an additional 4 h. The suspension was then filtered to give Nilotinib HBr form VI. The obtained product was dried in a vacuum oven (35 mmHg) at 40° C. for 3 days. The dried product was analyzed by PXRD and was found to be Nilotinib HBr form VI. The dried product was then subjected to additional drying at 60° C. in a vacuum oven for 15 hours, and then it was analyzed by PXRD and was found to be Nilotinib HBr form VI.

Workup

  1. stirringStirring
  2. temperatureto cool to room temperature by removal of the heat source
  3. stirringthe mixture was stirred at room temperature for an additional 4 h
  4. filtrationThe suspension was then filtered

Sources & evidence

ORD record
ord-df7d2ef2467b49dfb997f1d7b55913e0
Source dataset
uspto-grants-2015_07
Patent number
US09090598B2

Reaction notes

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