HCID 66670722, compound → HCID 46938058, compound

HRID 1517854Notes

Reaction equation

HRID 1517854 reaction equation
C(O[C:9]([N:11]([CH2:13][C:14]([O:16][C@H:17]([CH3:54])[CH2:18][N:19]1[C:23]([CH3:24])=[C:22]([C:25](=[O:46])[NH:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]3[C:43]4[C:38](=[CH:39][C:40]([O:44][CH3:45])=[CH:41][CH:42]=4)[N:37]=[CH:36][CH:35]=3)=[CH:29][N:28]=2)[C:21](=[O:47])[N:20]1[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:15])C)=O)C1C=CC=CC=1>CO.[Pd]>[CH3:9][NH:11][CH2:13][C:14]([O:16][C@H:17]([CH3:54])[CH2:18][N:19]1[C:23]([CH3:24])=[C:22]([C:25](=[O:46])[NH:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]3[C:43]4[C:38](=[CH:39][C:40]([O:44][CH3:45])=[CH:41][CH:42]=4)[N:37]=[CH:36][CH:35]=3)=[CH:29][N:28]=2)[C:21](=[O:47])[N:20]1[C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)=[O:15]

Participants

4

Reactant 1

HCID 66670722HCID 66670722, compound

Product 1

HCID 46938058HCID 46938058, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (R)-1-(4-(5-(7-methoxyquinolin-4-yloxy)pyridin-2-ylcarbamoyl)-2,3-dihydro-5-methyl-3-oxo-2-phenylpyrazol-1-yl)propan-2-yl 2-(N-benzyloxycarbonyl-N-methylamino)acetate (1.0 g, 1.4 mmol) in MeOH (100 mL) was added catalytic amount wet Pd/C (10%, ˜55% w/w water content, 10 mg) under N2 atmosphere. The suspension was degassed under vacuum and then purged with H2. The reaction mixture was stirred at rt for 20 minutes under H2 balloon. The mixture was filtered and the residue was washed with MeOH (35 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 (35 mL×3)

Sources & evidence

ORD record
ord-1ecbf7f1d91f476fa75da146b0a1e35c
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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