4-Methoxybenzenesulfonyl chloride → N-[1-(2',4',5-Trifluoro-1,1'-biphenyl-2-yl)ethyl]-4-methoxybenzenesulfonamide

HRID 2181909

Reaction equation

HRID 2181909 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]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[CH:28]([NH2:30])[CH3:29].C(N(CC)CC)C>>[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[CH:28]([NH:30][S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])[CH3:29]

Participants

4

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 224823821-(2',4',5-Trifluoro-1,1'-biphenyl-2-yl)ethylamine

Product 1

HCID 22482340N-[1-(2',4',5-Trifluoro-1,1'-biphenyl-2-yl)ethyl]-4-methoxybenzenesulfonamideYield 70%

Procedure

The title compound was prepared from 4-methoxybenzenesulfonyl chloride (146 mg, 0.7 mmol), 1-(-2′,4′,5-trifluoro-1,1′-biphenyl-2-yl)ethylamine (169 mg, 0.67 mmol), and triethylamine (187 μL, 1.3 mmol) according to the procedure and in the same manner as described in Example 105, step c. The product was 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 desired compound (197 mg, 70%) as a white solid;

Workup

  1. customThe product was purified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g)
  2. washeluting with a gradient of 30%-50% methyl tert-butyl ether in hexane (35 min)

Sources & evidence

ORD record
ord-dfd8cad47b7245c2af27b0850ed039c6
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Linked notes

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