4-(4-Pyridyloxy)benzenesulfonyl chloride → 5-Methyl-4-[4-(pyridin-4-yloxy)-benzenesulfonylamino]-biphenyl-3-carboxylic acid methyl ester

HRID 1883534Notes

Reaction equation

HRID 1883534 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[C:9]([CH3:12])[C:10]=1[NH2:11])=[O:4].[N:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[CH:21][CH:20]=1>N1C=CC=CC=1.O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[C:9]([CH3:12])[C:10]=1[NH:11][S:32]([C:29]1[CH:28]=[CH:27][C:26]([O:25][C:22]2[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=2)=[CH:31][CH:30]=1)(=[O:33])=[O:34])=[O:4]

Participants

5

Reactant 2

HCID 27352584-(4-Pyridyloxy)benzenesulfonyl chloride2×HCID 542075304-Amino-5-methyl-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 544530595-Methyl-4-[4-(pyridin-4-yloxy)-benzenesulfonylamino]-biphenyl-3-carboxylic acid methyl esterYield 90.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of 1.43 g (5.93 mmol) of the product of Example 40 in 20 mL of pyridine was added 1.98 g (6.52 mmol) 4-(pyridin-4-yloxy)-benzenesulfonyl chloride and the reaction was stirred overnight. Additional 4-(pyridin-4-yloxy)-benzenesulfonyl chloride (0.5 g, 1.6 mmol) was added twice over the next two days. The reaction was then diluted with water and extracted three times with dichloromethane. The organics were combined, washed with brine, dried over Na2SO4, concentrated in vacuo and chromatographed on silica gel using gradient elution (100% hexane to 100% ethyl acetate) to provide 5-methyl-4-[4-(pyridin-4-yloxy)-benzenesulfonylamino]-biphenyl-3-carboxylic acid methyl ester 2.54 g (90%) as a white solid. Electrospray Mass Spec: 475.2 (M+H)+

Workup

  1. extractionextracted three times with dichloromethane
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customchromatographed on silica gel using gradient elution (100% hexane to 100% ethyl acetate)

Sources & evidence

ORD record
ord-d9385a2b74e04c7daec4314f236b3d54
Source dataset
uspto-grants-2004_07
Patent number
US06762178B2

Reaction notes

Loading…