4-(Thiophen-2-yl)benzene-1-sulfonyl chloride → N-[5-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-4-(2-thienyl)benzenesulfonamide

HRID 130435Notes

Reaction equation

HRID 130435 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[CH:11][C:12]([O:16][CH3:17])=[C:13]([CH:15]=2)[NH2:14])[CH2:3]1.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>N1C=CC=CC=1>[CH3:8][C@H:6]1[NH:7][C@@H:2]([CH3:1])[CH2:3][N:4]([C:9]2[CH:10]=[CH:11][C:12]([O:16][CH3:17])=[C:13]([NH:14][S:29]([C:26]3[CH:25]=[CH:24][C:23]([C:19]4[S:18][CH:22]=[CH:21][CH:20]=4)=[CH:28][CH:27]=3)(=[O:30])=[O:31])[CH:15]=2)[CH2:5]1

Participants

4

Reactant 2

HCID 183877594-(Thiophen-2-yl)benzene-1-sulfonyl chlorideHCID 590070635-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)aniline

Product 1

HCID 25022506N-[5-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-4-(2-thienyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)aniline (D4) (200 mg, 0.85 mmol) in pyridine (5 ml) was treated 4-(2-thienyl)benzenesulfonyl chloride (WO 9827069) (258 mg, 1.0 mmol). The solution was stirred at room temperature for 24 hours and concentrated in vacuo. The residue was co-evaporated with methanol and toluene (×3). The residue was dissolved in dichloromethane and washed with saturated sodium bicarbonate solution. The organic phase was washed with water, brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (1:40 to 1:20 2M ammonia in methanol:dichloromethane) to afford the title product (E17). MS (ES+) m/e 458 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with saturated sodium bicarbonate solution
  4. washThe organic phase was washed with water, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (1:40 to 1:20 2M ammonia in methanol:dichloromethane)

Sources & evidence

ORD record
ord-8311f64446a9473b9fd337f09901ae40
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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