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

HRID 2181916Notes

Reaction equation

HRID 2181916 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]=[CH:18][C:17]([F:20])=[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]=[CH:18][C:17]([F:20])=[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 224822791-(2',5',5-Trifluoro-1,1'-biphenyl-2-yl)ethylamine

Product 1

HCID 22482378N-[1-(2',5',5-Trifluoro-1,1'-biphenyl-2-yl)ethyl]-4-methoxybenzenesulfonamideYield 91%

Procedure

The title compound was prepared from 4-methoxybenzenesulfonyl chloride (153 mg, 0.74 mmol), 1-(-2′,5′,5-trifluoro-1,1′-biphenyl-2-yl)ethylamine (177 mg, 0.70 mmol), and triethylamine (147 μL, 1.1 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 (259 mg, 91%) 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-5e7084eab9ce4a138321258104b49a5d
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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