Imatinib Mesylate → Imatinib

HRID 657459Notes

Reaction equation

HRID 657459 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:21][C:22]([C:24]2[CH:25]=[CH:26][C:27]([CH2:30][N:31]3[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]3)=[CH:28][CH:29]=2)=[O:23])=[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.CS(O)(=O)=O.C([O-])(O)=O.[Na+]>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:21][C:22]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][N:31]3[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH2:36]3)=[CH:26][CH:25]=2)=[O:23])=[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

Participants

4

Reactant 2

HCID 123596Imatinib Mesylate3×HCID 516892Sodium Bicarbonate

Product 1

HCID 5291Imatinib

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

The imatinib mesylate salt (1) (1.01 g, 1.71 mmol) prepared in Example 1 was added to 250 mL of dichloromethane to form a suspension of imatinib mesylate. 50 mL of 10% saturated aqueous NaHCO3 was added and mixed well with the suspension of imatinib mesylate in dichloromethane to produce the free base of imatinib in the organic layer (dichloromethane). The emulsion formed from the aqueous NaHCO3 and the dichloromethoane was removed by filtration, producing an organic layer of dichloromethane containing the imatinib as the free base and an aqueous layer. The organic layer of dicholomethane containing imatninb as the free base was separated from the aqueous layer. The organic layer was dried over Na2SO4/MgSO4. To isolate the imatinib free base, the organic layer (dichloromethane) was filtered to remove the Na2SO4/MgSO4 and then stipped off, producing a solid containing the free base of imatinib. Toluene was added to the solid containing imatinib free base and flash evaporated three times and then dried under vacuum to remove any residual water. The free base of imatinib was obtained as a white solid and used in example 3. The free base of imatinib exhibited 1H, 13C NMR and APCI data consistent with the structure. NMR assignments were based on a DQF-COSY experiment.

Workup

  1. customto form

Sources & evidence

ORD record
ord-fb7b222c6a554529acbae9fea0492800
Source dataset
uspto-grants-2011_12
Patent number
US08076097B2

Reaction notes

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