Water → HCID 15282102, compound

HRID 36189Notes

Reaction equation

HRID 36189 reaction equation
[H-].[Na+].[CH2:3]([C:7]1[N:8]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[S:26](=[O:33])(=[O:32])[NH:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:16][CH:15]=2)[C:9](=[O:12])[NH:10][N:11]=1)[CH2:4][CH2:5][CH3:6].[CH:34](I)([CH3:36])[CH3:35].O>CN(C=O)C>[CH2:3]([C:7]1[N:8]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[S:26](=[O:32])(=[O:33])[NH:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:18][CH:19]=2)[C:9](=[O:12])[N:10]([CH:34]([CH3:36])[CH3:35])[N:11]=1)[CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 103886375-n-Butyl-4-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 15282102HCID 15282102, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 54 mg (1.35 mmole) of sodium hydride (60% in oil) in 1 ml of dry DMF was added 200 mg (0.452 mmole) of 5-n-butyl-4-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step G). The resulting mixture was stirred under N2 at room temperature for 2 hours. Then 270 μL (460 mg, 2.70 mmole) of isopropyl iodide was added dropwise, and the orange mixture was stirred at room temperature overnight. Next, the mixture was treated with H2O and extracted 4× with ethyl acetate. The combined organic fractions were washed with brine, dried over MgSO4, and filtered. The filtrate was concentrated in vacuo, and the residue was flash chromatographed twice on silica gel (elution with 1.5% MeOH in CH2Cl2) to yield 106 mg (48%) of the title compound; satisfactory purity by TLC in 98.5:1.5 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 485 (M+1)+.

Workup

  1. stirringthe orange mixture was stirred at room temperature overnight
  2. extractionextracted 4× with ethyl acetate
  3. washThe combined organic fractions were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customchromatographed twice on silica gel (elution with 1.5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-e8a7d5cebe4449f08a4c95f90385911c
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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