2,5-Dichlorobenzenesulfonyl chloride → 2,5-Dichloro-N-cyclopentyl-N-[4-(1-hydroxy-3-phenyl-1-trifluoromethyl-prop-2-ynyl)-phenyl]-benzenesulfonamide

HRID 1791012Notes

Reaction equation

HRID 1791012 reaction equation
[CH:1]1([NH:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]([OH:26])([C:18]#[C:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[S:35](Cl)(=[O:37])=[O:36]>N1C=CC=CC=1>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[S:35]([N:6]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)[C:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:26])([C:14]([F:16])([F:17])[F:15])[C:18]#[C:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:9][CH:8]=1)(=[O:37])=[O:36]

Participants

4

Reactant 2

HCID 794012,5-Dichlorobenzenesulfonyl chlorideHCID 220425882-(4-Cyclopentylamino-phenyl)-1,1,1-trifluoro-4-phenyl-but-3-yn-2-ol

Product 1

HCID 220425732,5-Dichloro-N-cyclopentyl-N-[4-(1-hydroxy-3-phenyl-1-trifluoromethyl-prop-2-ynyl)-phenyl]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 53 mg of 2-(4-cyclopentylamino-phenyl)-1,1,1-trifluoro-4-phenyl-but-3-yn-2-ol (0.15 mmol) and 44 mg of 2,5-dichlorobenzenesulfonyl chloride (0.18 mmol) in 0.2 ml of pyridine was heated to 70° C. for 14 hours. After this time the reaction mixture was allowed to cool to room temperature, quenched by the addition of a saturated aqueous solution of ammonium chloride, and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica (hexanes:EtOAc, 4:1) to give the title compound. 1H-NMR (CDCl3) δ 1.36–1.58 (m, 6H), 1.97–2.07 (m, 2H), 4.73–4.78 (m, 1H), 7.18 (d, J=8.4 Hz, 2H), 7.37–7.55 (m, 7H), 7.76 (d, J=8.4 Hz, 2H), 7.84 (d, J=2.4 Hz, 1H). Mass Spectrum (CI+) m/e=590.0 (M+23).

Workup

  1. temperatureto cool to room temperature
  2. customquenched by the addition of a saturated aqueous solution of ammonium chloride
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by chromatography on silica (hexanes:EtOAc, 4:1)

Sources & evidence

ORD record
ord-a44c26cf9d6443bda601b2b6b77d0b6c
Source dataset
uspto-grants-2006_07
Patent number
US07071358B2

Reaction notes

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