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

HRID 2181892ノート

反応式

HRID 2181892 の反応式
[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]=[CH:25][CH:24]=[CH:23][C:22]=1[CH:27]([NH2:29])[CH3:28].C(N(CC)CC)C.O>C(#N)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:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])[CH3:28]

参加物

6

反応物 4

HCID 962WaterHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 224823761-[2-(2,4-Difluorophenyl)phenyl]ethan-1-amine

生成物 1

HCID 22482282N-[1-(2',4'-Difluoro-1,1'-biphenyl-2-yl)ethyl]4-methoxybenzenesulfonamide収率 78.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

4-Methoxybenzenesulfonyl chloride (341 mg, 1.7 mmol) was added to a solution of 1-(-2′,4′-difluoro-biphenyl-2-yl)ethylamine (350 mg, 1.5 mmol) and triethylamine (418 μL, 3 mmol) in acetonitrile. The reaction progress was monitored by LCMS and after 2 hours the reaction appeared to be complete. Water was added and the resulting solid was collected by filtration. The solid was dissolved in dichloromethane and 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 title compound (473 mg, 78%) as a white solid, m.p. 154-155° C.;

後処理

  1. filtrationthe resulting solid was collected by filtration
  2. dissolutionThe solid was dissolved in dichloromethane
  3. custompurified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g)
  4. washeluting with a gradient of 30%-50% methyl tert-butyl ether in hexane (35 min)

出典と根拠

ORDレコード
ord-4258bcd178464c3da239bfe95486b7d3
出典データセット
uspto-grants-2005_05
特許番号
US06894061B2

反応ノート

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