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

HRID 496409ノート

反応式

HRID 496409 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b11c29e603ac4768a4bf77c1c904b382
出典データセット
uspto-grants-2005_09
特許番号
US06943183B2

反応ノート

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