Triethylamine → HCID 90022431, compound

HRID 1772854Notes

Reaction equation

HRID 1772854 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([S:18][C:19]([F:22])([F:21])[F:20])[CH:13]=1)(=[O:10])=[O:9].[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24].C(N(CC)CC)C>CN(C=O)C>[F:20][C:19]([S:18][C:14]1[CH:13]=[C:12]([N:11]2[C:23](=[O:24])[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8]2(=[O:10])=[O:9])[CH:17]=[CH:16][CH:15]=1)([F:22])[F:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 90030803HCID 90030803, compound

Product 1

HCID 90022431HCID 90022431, compoundYield 140%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-amino-N-{3-[(trifluoromethyl)sulfanyl]phenyl}benzenesulfonamide (52 mg, 0.15 mmol), 1,1′-carbonyldiimidazole (97 mg, 0.60 mmol) and triethylamine (41 μL, 0.30 mmol) in DMF (0.75 mL) was heated in a sealed tube for 5 h at 100° C. After concentration in vacuo, DCM and 1M aqueous HCl were added, the phases were separated, the organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Purification by flash chromatography, eluting with 3% MeOH in DCM yielded the title compound (45 mg, 0.21 mmol).

Workup

  1. concentrationAfter concentration in vacuo, DCM and 1M aqueous HCl
  2. additionwere added
  3. customthe phases were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography
  9. washeluting with 3% MeOH in DCM

Sources & evidence

ORD record
ord-b0849b24f5f44cb99d76a27d0636ca0d
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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