Maleic Acid → (R)-1-(4-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenylcarbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl 2-(methylamino)acetate maleate

HRID 1517830Notes

Reaction equation

HRID 1517830 reaction equation
[CH3:1][NH:2][CH2:3][C:4]([O:6][C@H:7]([CH3:45])[CH2:8][N:9]1[C:13]([CH3:14])=[C:12]([C:15](=[O:37])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[C:33]4[C:28](=[CH:29][C:30]([O:34][CH3:35])=[CH:31][CH:32]=4)[N:27]=[CH:26][CH:25]=3)=[C:19]([F:36])[CH:18]=2)[C:11](=[O:38])[N:10]1[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:5].[C:46]([OH:53])(=[O:52])/[CH:47]=[CH:48]\[C:49]([OH:51])=[O:50]>CCOC(C)=O.CO>[C:46]([OH:53])(=[O:52])/[CH:47]=[CH:48]\[C:49]([OH:51])=[O:50].[CH3:1][NH:2][CH2:3][C:4]([O:6][C@H:7]([CH3:45])[CH2:8][N:9]1[C:13]([CH3:14])=[C:12]([C:15](=[O:37])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[C:33]4[C:28](=[CH:29][C:30]([O:34][CH3:35])=[CH:31][CH:32]=4)[N:27]=[CH:26][CH:25]=3)=[C:19]([F:36])[CH:18]=2)[C:11](=[O:38])[N:10]1[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:5]

Participants

5

Reactant 2

HCID 444266Maleic AcidHCID 46937772(R)-1-(4-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenylcarbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl 2-(methylamino)acetate

Product 1

HCID 66669919(R)-1-(4-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenylcarbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl 2-(methylamino)acetate maleate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution (R)-1-(4-(4-(7-methoxyquinolin-4-yloxy)-3-fluorophenylcarbamoyl)-2,3-dihydro-5-methyl-3-oxo-2-phenylpyrazol-1-yl)propan-2-yl 2-(methylamino)acetate (82.3 mg, 0.134 mmol) in a mixture of EtOAc (10 mL) and MeOH (10 mL) was added maleic acid (31.1 mg, 0.268 mmol, Shanghai San'aisi Reagent Co., Ltd). After stirring for 40 min, the reaction mixture was concentrated in vacuo. The residue was recrystallized in a mixture of MeOH (2 mL)/EtOAc (10 mL). The solid was collected by filtration, washed with EtOAc (5 mL×3) and dried under vacuum overnight. The title compound was obtained as a yellow solid (60.2 mg, 53%).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was recrystallized in a mixture of MeOH (2 mL)/EtOAc (10 mL)
  3. filtrationThe solid was collected by filtration
  4. washwashed with EtOAc (5 mL×3)
  5. customdried under vacuum overnight

Sources & evidence

ORD record
ord-dcb1404c1929457f9fe2d4377705c319
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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