Acetonitrile → N-[4'-[[1-Ethyl-5-formyl-3-propyl-1H-pyrazol-4-yl]methyl][1,1'-biphenyl]-2-yl]trifluoromethanesulphonamide

HRID 274598Notes

Reaction equation

HRID 274598 reaction equation
[CH2:1]([N:3]1[C:7]([CH2:8][OH:9])=[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[NH:23][S:24]([C:27]([F:30])([F:29])[F:28])(=[O:26])=[O:25])=[CH:13][CH:12]=2)[C:5]([CH2:31][CH2:32][CH3:33])=[N:4]1)[CH3:2].C[N+]1([O-])CCOCC1.C(#N)C>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:1]([N:3]1[C:7]([CH:8]=[O:9])=[C:6]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[NH:23][S:24]([C:27]([F:29])([F:28])[F:30])(=[O:25])=[O:26])=[CH:15][CH:16]=2)[C:5]([CH2:31][CH2:32][CH3:33])=[N:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 82029Methyl morpholine oxideHCID 20093324N-[4'-[[1-Ethyl-5-(hydroxymethyl)-3-propyl-1H-pyrazol-4-yl]methyl][1,1'-biphenyl]-2-yl]trifluoromethanesulphonamide

Product 1

HCID 20093388N-[4'-[[1-Ethyl-5-formyl-3-propyl-1H-pyrazol-4-yl]methyl][1,1'-biphenyl]-2-yl]trifluoromethanesulphonamideYield 70.1%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Tetra-n-propylammonium perruthenate (46 mg) was added to a mixture of the product of Example 86 (630 mg), N-methylmorpholine N-oxide (0.46 g) and 4A molecular sieves (2.5 g) in dichloromethane (10 ml) and dry acetonitrile (10 ml) and the reaction left for 5 min. The reaction was filtered, solvent removed in vacuo and the residue adsorbed onto silica. The material was purified by chromatography eluting with System A (4:1) to give the title compound as a yellow gum (0.44 g).

Workup

  1. filtrationThe reaction was filtered
  2. customsolvent removed in vacuo
  3. customThe material was purified by chromatography
  4. washeluting with System A (4:1)

Sources & evidence

ORD record
ord-9ed0903f386546c38e62339571b75e81
Source dataset
uspto-grants-1995_02
Patent number
US05389659

Reaction notes

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