HCID 24851818, compound → HCID 24853176, compound

HRID 500555Notes

Reaction equation

HRID 500555 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([C:15]2[N:19]([CH3:20])[C:18]([O:21][CH:22]([C:24]3[CH:28]=[C:27]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=4)[O:26][N:25]=3)[CH3:23])=[N:17][N:16]=2)[CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1>C(O)C.[Pd].ClCCl>[Cl:35][C:31]1[CH:30]=[C:29]([C:27]2[O:26][N:25]=[C:24]([CH:22]([O:21][C:18]3[N:19]([CH3:20])[C:15]([C:13]4[CH:12]=[CH:11][NH:10][C:9](=[O:8])[CH:14]=4)=[N:16][N:17]=3)[CH3:23])[CH:28]=2)[CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 1

HCID 24851818HCID 24851818, compound

Product 1

HCID 24853176HCID 24853176, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound of example 35.1 (125 mg, 0.256 mmol) was stirred in ethanol (2 mL). Palladium on carbon (10%, 50 mg) was added and the reaction was stirred under hydrogen (balloon pressure) overnight. The reaction mixture was then diluted with dichloromethane and filtered to remove the palladium catalyst. The filtrate was concentrated, then chromatographed in 10% methanol in ethyl acetate to yield the desired product (38.5 mg, 38%).

Workup

  1. filtrationfiltered
  2. customto remove the palladium catalyst
  3. concentrationThe filtrate was concentrated
  4. customchromatographed in 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-a93f41b8699045c7999178beb229ede2
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

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