Oxalic Acid → HCID 86688199, compound

HRID 1428317Notes

Reaction equation

HRID 1428317 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.[C:45]([OH:50])(=[O:49])[C:46]([OH:48])=[O:47]>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.[C:45]([O-:50])(=[O:49])[C:46]([O-:48])=[O:47]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 6228DimethylformamideHCID 644241Nilotinib

Product 1

HCID 86688199HCID 86688199, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

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 at that temperature for 30 min. A solution of oxalic acid (1.38 g, 15.33 mmol, 2.03 mol eq) in EtOH abs. (10 mL 2.5V) was added in one portion and a suspension was obtained. Stirring of the suspension was continued for 1 h at 80° C. The reaction vessel was then allowed to cool to ambient temperature by removal of the reaction vessel from the heating source, and the mixture was stirred at ambient temperature for 6 h. Another 20 mL EtOH abs. was added during this time to improve the stirring. A yellow precipitate formed and was isolated by vacuum filtration and dried in a vacuum oven (35 mmHg) at 70° C. for 24 h to give Nilotinib oxalate form I (5.3 g) as a yellow solid. The sample was analyzed by PXRD (Bruker X-Ray powder diffractometer model D8 advance equipped with lynxEye). Di oxalate salt was obtained according to assay determination.

Workup

  1. customat room temperature
  2. addition(10 mL 2.5V) was added in one portion
  3. customa suspension was obtained
  4. stirringStirring of the suspension
  5. waitwas continued for 1 h at 80° C
  6. temperatureto cool to ambient temperature by removal of the reaction vessel from the heating source
  7. stirringthe mixture was stirred at ambient temperature for 6 h
  8. additionwas added during this time
  9. customA yellow precipitate formed
  10. customwas isolated by vacuum filtration
  11. customdried in a vacuum oven (35 mmHg) at 70° C. for 24 h

Sources & evidence

ORD record
ord-c4fc5cd267ba4d6d9e27df1667e86f9a
Source dataset
uspto-grants-2015_01
Patent number
US08937082B2

Reaction notes

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