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

HRID 651077Notes

Reaction equation

HRID 651077 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-a7a9c7459f0e43b585dc4f7401f2b13f
Source dataset
uspto-grants-2001_08
Patent number
US06277885B1

Reaction notes

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