HCID 10323190, compound → HCID 70143915, compound

HRID 1019249Notes

Reaction equation

HRID 1019249 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:21](SC)[N:20]=[C:19]2[CH2:30][CH2:31][CH2:32][CH3:33])=[CH:13][CH:12]=1)(=[O:4])=[O:3]>C(O)C.[Ni]>[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][N:20]=[C:19]2[CH2:30][CH2:31][CH2:32][CH3:33])=[CH:13][CH:12]=1)(=[O:3])=[O:4]

Participants

4

Reactant 1

HCID 10323190HCID 10323190, compound

Product 1

HCID 70143915HCID 70143915, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent

Procedure

244 mg of ethyl 1-[[2′-(aminosulfonyl)(1,1′-biphenyl)-4-yl]methyl]-2-butyl-4-(methylthio)-1-H-imidazole-5-carboxylate (J. Med. Chem. 1995, 38, 2357) are dissolved in 10 ml of ethanol and 200 mg of Raney nickel are added. The mixture is then refluxed for 6 h, a further 200 mg of Raney nickel are added and it is again refluxed for 3 h. The residue is filtered off and the solvent is removed in vacuo. 200 mg of a colorless oil are obtained.

Workup

  1. temperatureThe mixture is then refluxed for 6 h
  2. temperatureit is again refluxed for 3 h
  3. filtrationThe residue is filtered off
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-bc265eefc25246bbb6c7d0b9977fa99e
Source dataset
uspto-grants-2002_11
Patent number
US06486189B2

Reaction notes

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