(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-((benzyloxycarbonyl)(methyl)-amino)acetate → (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

HRID 1517829Notes

Reaction equation

HRID 1517829 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]4[C:24](=[O:54])[N:25]([C:48]5[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=5)[N:26]([CH2:29][C@H:30]([O:32][C:33](=[O:47])[CH2:34][N:35](C(OCC5C=CC=CC=5)=O)[CH3:36])[CH3:31])[C:27]=4[CH3:28])=[O:22])=[CH:16][C:15]=3[F:55])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1>CCOC(C)=O.CO.[Pd]>[CH3:36][NH:35][CH2:34][C:33]([O:32][C@H:30]([CH3:31])[CH2:29][N:26]1[C:27]([CH3:28])=[C:23]([C:21](=[O:22])[NH:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][C:7]3[C:6]4[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[N:10]=[CH:9][CH:8]=3)=[C:15]([F:55])[CH:16]=2)[C:24](=[O:54])[N:25]1[C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)=[O:47]

Participants

5

Reactant 1

HCID 66670738(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-((benzyloxycarbonyl)(methyl)-amino)acetate

Product 1

HCID 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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (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-(N-benzyloxycarbo-nyl-N-methylamino)acetate (1.404 g, 1.876 mmol) in a mixture of EtOAc (100 mL) and MeOH (100 mL) was added catalytic amount of Pd/C (10%, ˜55% w/w water content, 100 mg) under N2 atmosphere. The suspension was degassed under vacuum and then purged with H2. The reaction mixture was stirred at rt for 1 h under H2 balloon. The mixture was filtered and the residue was washed with MeOH (50 mL×3). The filtrate used for the next step immediately.

Workup

  1. customThe suspension was degassed under vacuum
  2. custompurged with H2
  3. filtrationThe mixture was filtered
  4. washthe residue was washed with MeOH (50 mL×3)

Sources & evidence

ORD record
ord-26592ac853aa4c04b6bea677ca4714ec
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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