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

HRID 2181895Notes

Reaction equation

HRID 2181895 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]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH:27]([NH2:29])[CH3:28].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]=[CH:25][CH:24]=[CH:23][C:22]=1[CH:27]([NH:29][S:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:11])=[O:10])[CH3:28]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 27375043-Methoxybenzenesulfonyl chlorideHCID 224823761-[2-(2,4-Difluorophenyl)phenyl]ethan-1-amine

Product 1

HCID 22482284N-[1-(2',4'-Difluoro-1,1'-biphenyl-2-yl)ethyl]-3-methoxybenzenesulfonamide

Procedure

The title compound was prepared from 3-methoxybenzenesulfonyl chloride (341 mg, 1.7 mmol), 1-(-2′,4′-difluoro-biphenyl-2-yl)ethylamine (350 mg, 1.5 mmol), and triethylamine (418 μL, 3 mmol) according to the procedure and in the same manner as described in Example 105, step c. The solid 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), and the product (473 mg, 78%) isolated as a white solid, m.p. 127.5-129° C.;

Workup

  1. customThe solid 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-3eefea47c2a44312a5f1a1ad861e7214
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

Loading…