Dimethylformamide → HCID 67410238, compound

HRID 2245266Notes

Reaction equation

HRID 2245266 reaction equation
C([N:8]1[CH2:12][CH:11]([OH:13])[CH:10]([NH:14][C:15]([C:17]2[C:21]([CH3:22])=[C:20](/[CH:23]=[C:24]3\[C:25](=[O:34])[NH:26][C:27]4[C:32]\3=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[NH:19][C:18]=2[CH3:35])=[O:16])[CH2:9]1)C1C=CC=CC=1.CN(C=O)C>C(O)(=O)C.[Pd].CO>[OH:13][CH:11]1[CH2:12][NH:8][CH2:9][CH:10]1[NH:14][C:15]([C:17]1[C:21]([CH3:22])=[C:20](/[CH:23]=[C:24]2\[C:25](=[O:34])[NH:26][C:27]3[C:32]\2=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[NH:19][C:18]=1[CH3:35])=[O:16]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 592159265-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (1-benzyl-4-hydroxy-pyrrolidin-3-yl)-amide

Product 1

HCID 67410238HCID 67410238, compoundYield 78.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of Example 26 (283.7 mg, 0.59 mmol), 10% Pd/C (282 mg) and acetic acid (3 drops) in 30 mL of [DMF:MeOH=1:1] was stirred at r.t. under H2 atmosphere. After the reaction was complete as detected by LC/MS, the catalyst was filtered off and the filtrate was evaporated to dryness. The residue was triturated with ethanol to provide 5-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (4-hydroxy-pyrrolidin-3-yl)-amide (178 mg, 67%).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated to dryness
  3. customThe residue was triturated with ethanol

Sources & evidence

ORD record
ord-694d9696c077495389e8078a5acb1da9
Source dataset
uspto-grants-2010_03
Patent number
US07683057B2

Reaction notes

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