Triethylamine → N-[1-(2',5',5-Trifluoro-1,1'-biphenyl-2-yl)ethyl]-3-methoxybenzenesulfonamide

HRID 2181918

Reaction equation

HRID 2181918 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.[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:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:11])=[O:10])[CH3:29]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 27375043-Methoxybenzenesulfonyl chlorideHCID 224822791-(2',5',5-Trifluoro-1,1'-biphenyl-2-yl)ethylamine

Product 1

HCID 22482389N-[1-(2',5',5-Trifluoro-1,1'-biphenyl-2-yl)ethyl]-3-methoxybenzenesulfonamideYield 100%

Procedure

The title compound was prepared from 3-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 uL, 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 (295 mg, 100%) 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-4f2e9c43accc4ec891d7b521905263d2
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Linked notes

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