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molecular formula C29H31N7O B000729 Imatinib CAS No. 152459-95-5

Imatinib

Cat. No. B000729
M. Wt: 493.6 g/mol
InChI Key: KTUFNOKKBVMGRW-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US08076097B2

Procedure details

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.
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Quantity
1.01 g
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
50 mL
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Five
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Five
Quantity
250 mL
Type
solvent
Reaction Step Six

Identifiers

REACTION_CXSMILES
[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 |f:0.1,2.3|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
ClCCl
Step Two
Name
Quantity
1.01 g
Type
reactant
Smiles
CC=1C=CC(=CC1NC=2N=CC=C(N2)C=3C=CC=NC3)NC(=O)C=4C=CC(=CC4)CN5CCN(CC5)C.CS(=O)(=O)O
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC=1C=CC(=CC1NC=2N=CC=C(N2)C=3C=CC=NC3)NC(=O)C=4C=CC(=CC4)CN5CCN(CC5)C.CS(=O)(=O)O
Step Four
Name
Quantity
50 mL
Type
reactant
Smiles
C(=O)(O)[O-].[Na+]
Step Five
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC=1C=CC(=CC1NC=2N=CC=C(N2)C=3C=CC=NC3)NC(=O)C=4C=CC(=CC4)CN5CCN(CC5)C.CS(=O)(=O)O
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
ClCCl
Step Six
Name
Quantity
250 mL
Type
solvent
Smiles
ClCCl

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
to form

Outcomes

Product
Name
Type
product
Smiles
CC=1C=CC(=CC1NC=2N=CC=C(N2)C=3C=CC=NC3)NC(=O)C=4C=CC(=CC4)CN5CCN(CC5)C

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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