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

HRID 2181898Notes

Reaction equation

HRID 2181898 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[S:11](Cl)(=[O:13])=[O:12].[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:29]([NH2:31])[CH3:30].C(N(CC)CC)C>>[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:29]([NH:31][S:11]([C:4]1[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=1[O:2][CH3:1])(=[O:13])=[O:12])[CH3:30]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 27346262,4-Dimethoxybenzenesulfonyl chlorideHCID 224823761-[2-(2,4-Difluorophenyl)phenyl]ethan-1-amine

Product 1

HCID 22482306N-[1-(2',4'-Difluoro-1,1'-biphenyl-2-yl)ethyl]-2,4-dimethoxybenzenesulfonamideYield 69.2%

Procedure

The title compound was prepared from 2,4-dimethoxybenzenesulfonyl chloride (473 mg, 2.0 mmol), 1-(2′,4′-difluoro-1,1′-biphenyl-2-yl)ethylamine (466 mg, 2.0 mmol), and triethylamine (334 μL, 2.2 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® 40Mi column of prepacked column of silica gel (90 g), eluting with a gradient of 30%-50% methyl tert-butyl ether in hexane (35 min), to afford the desired compound (600 mg, 69%) as a white solid;

Workup

  1. customThe product was purified by preparative liquid chromatography on a Biotage® 40Mi column of prepacked column of 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-0bfb11f44c824c00af81d3dff6dec8ec
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

Loading…