Methanesulfonyl chloride → HCID 21099526, compound

HRID 1351695Notes

Reaction equation

HRID 1351695 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([S:17]([C:20]3[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=3[CH2:22][NH2:23])(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>[OH-].[Na+].ClCCl>[F:2][C:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([S:17]([C:20]3[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=3[CH2:22][NH:23][S:29]([CH3:28])(=[O:31])=[O:30])(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 21099442HCID 21099442, compound

Product 1

HCID 21099526HCID 21099526, compoundYield 22.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

[2-({4-[(E)-2-(4-Fluorophenyl)vinyl]phenyl}sulfonyl)benzyl]amine hydrochloride (Example 178, 120 mg, 0.3 mmol) was added to a rapidly stirred mixture of methanesulfonyl chloride (50 μL, 0.6 mmol) in 1M sodium hydroxide (3 mL) and dichloromethane (3 mL). After 30 minutes, further methanesulfonyl chloride (100 μL, 1.2 mmol) and 4M sodium hydroxide (1 mL) were added and the reaction stirred for 30 minutes. The layers were separated and the organic layer washed with 1N HCl, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 60% ethyl acetate/isohexane to give the title compound as a white solid (30 mg, 22%). δH (500 MHz, d6 DMSO): 8.10 (1H, d, J=7.9 Hz), 7.90 (2H, d, J=8.4 Hz), 7.80 (2H, d, J=8.4 Hz), 7.75–7.67 (4H, m), 7.59 (1H, t, J=7.3 Hz), 7.55 (1H, s), 7.44 (1H, d, J=16.4 Hz), 7.29 (1H, d, J=16.5 Hz), 7.22 (2H, t, J=8.8 Hz), 4.44 (2H, s), 2.89 (3H, s).

Workup

  1. customThe layers were separated
  2. washthe organic layer washed with 1N HCl
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica
  6. washeluting with 60% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-9bcdff2843844913bf6ca1ddd5775f57
Source dataset
uspto-grants-2007_05
Patent number
US07217740B2

Reaction notes

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