Triethylamine → N-[1-(4'-chloro-2'-fluoro-1,1'-biphenyl-2-yl)ethyl]-3-methoxybenzenesulfonamide

HRID 2181927Notes

Reaction equation

HRID 2181927 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9](Cl)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH:26]([NH2:28])[CH3:27])=[C:16]([F:29])[CH:15]=1.C(N(CC)CC)C>C(#N)C>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH:26]([NH:28][S:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)(=[O:11])=[O:10])[CH3:27])=[C:16]([F:29])[CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27375043-Methoxybenzenesulfonyl chlorideHCID 224823611-(4'-Chloro-2'-fluoro-biphenyl-2-yl)-ethylamine

Product 1

HCID 22482365N-[1-(4'-chloro-2'-fluoro-1,1'-biphenyl-2-yl)ethyl]-3-methoxybenzenesulfonamideYield 103.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

3-Methoxybenzenesulfonyl chloride (331 mg, 1.6 mmol) was added to a solution of 1-(4′-chloro-2′-fluoro-1,1′-biphenyl-2-yl)ethylamine (400 mg, 1.6 mmol) and triethylamine (246 μL, 1.7 mmol) in acetonitrile. The reaction was mixed at room temperature for 24 hours, afterwhich the acetonitrile was removed in vacuo. The remaining solid was dissolved in dichloromethane and purified by preparative liquid chromatogrpahy on a Biotage® 40 Mi column of prepacked silica gel (90 g), eluting with a gradient of 5%-50% methyl tert-butyl ether in hexane (35 min), to afford the the desired product (694 mg, 99%) as a white solid;

Workup

  1. customwas removed in vacuo
  2. dissolutionThe remaining solid was dissolved in dichloromethane
  3. custompurified by preparative liquid chromatogrpahy on a Biotage® 40 Mi column of prepacked silica gel (90 g)
  4. washeluting with a gradient of 5%-50% methyl tert-butyl ether in hexane (35 min)

Sources & evidence

ORD record
ord-b214738d486547c9bd54ab946152c525
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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