Imatinib
货号 B000729
分子量: 493.6 g/mol
InChI 键: KTUFNOKKBVMGRW-UHFFFAOYSA-N
注意: 仅供研究使用。不适用于人类或兽医用途。
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.
Identifiers
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REACTION_CXSMILES
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[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|
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Inputs
Step One
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Name
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Quantity
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0 (± 1) mol
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Type
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solvent
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Smiles
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ClCCl
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Step Two
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Name
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Quantity
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1.01 g
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Type
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reactant
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Smiles
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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
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Step Three
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Name
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Quantity
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0 (± 1) mol
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Type
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reactant
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Smiles
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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
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Step Four
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Name
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Quantity
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50 mL
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Type
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reactant
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Smiles
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C(=O)(O)[O-].[Na+]
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Step Five
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Name
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Quantity
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0 (± 1) mol
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Type
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reactant
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Smiles
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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
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Name
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Quantity
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0 (± 1) mol
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Type
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solvent
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Smiles
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ClCCl
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Step Six
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Name
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Quantity
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250 mL
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Type
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solvent
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Smiles
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ClCCl
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Conditions
Other
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Conditions are dynamic
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1
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Details
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See reaction.notes.procedure_details.
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Workups
CUSTOM
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Type
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CUSTOM
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Details
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to form
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Outcomes
Product
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Name
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Type
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product
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Smiles
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CC=1C=CC(=CC1NC=2N=CC=C(N2)C=3C=CC=NC3)NC(=O)C=4C=CC(=CC4)CN5CCN(CC5)C
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Source
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Source
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Open Reaction Database (ORD) |
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Description
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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. |
