HCID 67245452, compound → HCID 67246082, compound

HRID 2425110Notes

Reaction equation

HRID 2425110 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([Br:11])=[C:6]([S:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=2[N+:23]([O-])=O)(=[O:14])=[O:13])[CH:5]=1>CN(C)C=O.[Ni]>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([Br:11])=[C:6]([S:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=2[NH2:23])(=[O:14])=[O:13])[CH:5]=1

Participants

4

Reactant 1

HCID 67245452HCID 67245452, compound

Product 1

HCID 67246082HCID 67246082, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

Activated Raney-Nickel was added to a solution of compound of Example 37c (1.50 g, 3.46 mmol) in dimethylformamide (100 mL). The reaction mixture was subjected to hydrogenation (25 psi pressure) for 2 h. Catalyst was filtered-off, washed with dimethylformamide and concentrated to obtain the crude product, which was then purified by column chromatography (silica gel, 30% ethyl acetate in pet. ether 60-80° C.) to obtain the title compound. Yield: 0.785 g, (56.07%). MS: m/e (ES+) 433 (M+1).

Workup

  1. washwashed with dimethylformamide
  2. concentrationconcentrated
  3. customto obtain the crude product, which
  4. customwas then purified by column chromatography (silica gel, 30% ethyl acetate in pet. ether 60-80° C.)

Sources & evidence

ORD record
ord-6398e854385a4a1dac06b59d5729c796
Source dataset
uspto-grants-2011_06
Patent number
US07964631B2

Reaction notes

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