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

HRID 2181892노트

반응식

HRID 2181892 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.;

후처리

  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)

출처 및 근거

ORD 기록
ord-4258bcd178464c3da239bfe95486b7d3
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06894061B2

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