Pyridine → N-[2-((S)-2-Imidazol-1-yl-1-phenyl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yl]-benzenesulfonamide

HRID 496409노트

반응식

HRID 496409 반응식
[NH2:1][C:2]1[C:11]([O:12][C@@H:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:26].N1C=CC=CC=1.[C:33]1([S:39](Cl)(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(Cl)Cl>[N:15]1([CH2:14][C@H:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:12][C:11]2[CH:10]=[CH:9][C:8]3[C:7](=[O:26])[CH2:6][CH2:5][CH2:4][C:3]=3[C:2]=2[NH:1][S:39]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)(=[O:41])=[O:40])[CH:19]=[CH:18][N:17]=[CH:16]1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 600298675-Amino-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

생성물 1

HCID 60029933N-[2-((S)-2-Imidazol-1-yl-1-phenyl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yl]-benzenesulfonamide수율 81.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 5-amino-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (100 mg, 0.288 mmol) in CH2Cl2 (2 mL) was added pyridine (47 mL, 0.576 mmol, 2 equiv) followed by benzenesulfonyl chloride (44 μL, 0.345 mmol, 1.2 equiv). The reaction was allowed to stir overnight at RT. The reaction was diluted with CH2Cl2, washed with saturated aqueous NH4Cl and brine, dried over MgSO4 to give an oil. Purification by chromatography (4% MeOH/CH2Cl2) gave the title compound as a white foam (114 mg, 0.234 mmol, 81%). The structure was confirmed by NMR and mass spectrometry. MS m/z 488 (M++H).

후처리

  1. washwashed with saturated aqueous NH4Cl and brine
  2. dry with materialdried over MgSO4
  3. customto give an oil
  4. customPurification by chromatography (4% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-b11c29e603ac4768a4bf77c1c904b382
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06943183B2

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