Potassium Carbonate → HCID 19024436, compound

HRID 1033802Notes

Reaction equation

HRID 1033802 reaction equation
[CH2:1]([N:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[S:22](=[O:29])(=[O:28])[NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:12][CH:11]=1)[C:6](Cl)=[O:7])[CH2:2][CH2:3][CH3:4].[F:30][C:31]([F:40])([F:39])[C:32]1[C:37]([OH:38])=[CH:36][CH:35]=[CH:34][CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([N:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[S:22](=[O:28])(=[O:29])[NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:12][CH:11]=1)[C:6](=[O:7])[O:38][C:37]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:31]([F:39])([F:40])[F:30])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 679582-TrifluoromethylphenolHCID 19024454HCID 19024454, compound

Product 1

HCID 19024436HCID 19024436, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 171 mg (0.391 mmole) of N-butyl-N-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]carbamoyl chloride (from Step F), 63.9 mg (0.394 mmole) of α,α,α-trifluoro-o-cresol, 66 mg (0.48 mmole) of anhydrous potassium carbonate, and 3 mL of DMF was stirred under N2 at 90° C. overnight. The cooled mixture was partitioned between 20 mL of 2N HCl and 20 mL of EtOAc. The organic layer was washed with H2O (2×30 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The residual oil was flash chromatographed on silica gel (gradient elution with 20-35% EtOAc in hexane to yield 37.4 mg (17%) of the title compound as a yellow oil, homogeneous by TLC in 3:1 hexane-EtOAc; FAB-MS m/e 562 (M+1)+. The 1H NMR spectrum indicated the presence of two rotameric forms.

Workup

  1. customThe cooled mixture was partitioned between 20 mL of 2N HCl and 20 mL of EtOAc
  2. washThe organic layer was washed with H2O (2×30 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel (
  7. washgradient elution with 20-35% EtOAc in hexane

Sources & evidence

ORD record
ord-9b42774326db4c18b6c63b3fed013d68
Source dataset
uspto-grants-1994_05
Patent number
US05312820

Reaction notes

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