HCID 54055502, compound → HCID 18681167, compound

HRID 276064Notes

Reaction equation

HRID 276064 reaction equation
[C:1]1([S:7]([NH:10][C:11](=[O:32])[CH:12]=[CH:13][C:14]2[CH:15]=[CH:16][C:17]3[N:21]=[C:20]([CH3:22])[N:19]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[Cl:30])[C:18]=3[CH:31]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>[Pd].C(O)C>[C:1]1([S:7]([NH:10][C:11](=[O:32])[CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]3[N:21]=[C:20]([CH3:22])[N:19]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[Cl:30])[C:18]=3[CH:31]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 54055502HCID 54055502, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18681167HCID 18681167, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5% Palladium on carbon (0.500 g) was added to a solution of 0.607 g of N-benzenesulfonyl-1-(2-chlorobenzyl)-2-methylbenzimidazole-6-acrylamide in 150 ml of ethanol, and the mixture was stirred in a hydrogen atmosphere at room temperature for 43 hours. The solid material was separated through filtration, and the filtrate was concentrated. The residue was dissolved in a mixed solution of a 20% potassium hydrogencarbonate aqueous solution and methanol, and was adjusted to a pH of from 5 to 6 with 10% hydrochloric acid. The crystals precipitated were separated through filtration, and was dried to give 0.250 g of N-benzenesulfonyl-3-[1-(2-chlorobenzyl)-2-methylbenzimidazol-6-yl]propionamide (266).

Workup

  1. customThe solid material was separated through filtration
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in a mixed solution of a 20% potassium hydrogencarbonate aqueous solution and methanol
  4. customThe crystals precipitated
  5. customwere separated through filtration
  6. customwas dried

Sources & evidence

ORD record
ord-1ad2e96828cd4f868cf4117d3170c693
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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