Water → N-[1-(2',4'-Difluoro-1,1'-biphenyl-2-yl)ethyl]4-methoxybenzenesulfonamide

HRID 2181892Notes

Reaction equation

HRID 2181892 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH:27]([NH2:29])[CH3:28].C(N(CC)CC)C.O>C(#N)C>[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH:27]([NH:29][S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 224823761-[2-(2,4-Difluorophenyl)phenyl]ethan-1-amine

Product 1

HCID 22482282N-[1-(2',4'-Difluoro-1,1'-biphenyl-2-yl)ethyl]4-methoxybenzenesulfonamideYield 78.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Methoxybenzenesulfonyl chloride (341 mg, 1.7 mmol) was added to a solution of 1-(-2′,4′-difluoro-biphenyl-2-yl)ethylamine (350 mg, 1.5 mmol) and triethylamine (418 μL, 3 mmol) in acetonitrile. The reaction progress was monitored by LCMS and after 2 hours the reaction appeared to be complete. Water was added and the resulting solid was collected by filtration. The solid was dissolved in dichloromethane and purified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g), eluting with a gradient of 30%-50% methyl tert-butyl ether in hexane (35 min), to afford the title compound (473 mg, 78%) as a white solid, m.p. 154-155° C.;

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. dissolutionThe solid was dissolved in dichloromethane
  3. custompurified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g)
  4. washeluting with a gradient of 30%-50% methyl tert-butyl ether in hexane (35 min)

Sources & evidence

ORD record
ord-4258bcd178464c3da239bfe95486b7d3
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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