Sodium hydride → 1-(2-{4-[2-(4-Methanesulfonyl-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenoxy}-ethyl)-azepine Hydrochloride

HRID 732789ノート

反応式

HRID 732789 の反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=3)[C:12]=2[O:23][C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.[N:32](=[CH:40][CH2:41]Cl)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][Cl:39].[H-].[Na+]>CN(C)C=O>[ClH:39].[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=3)[C:12]=2[O:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH2:41][CH2:40][N:32]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=[CH:33]3)=[CH:28][CH:29]=2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 534452772-(hexamethyleneimino)ethyl chloride HClHCID 685159634-[2-(4-Methanesulfonyl-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenol

生成物 1

HCID 685159301-(2-{4-[2-(4-Methanesulfonyl-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenoxy}-ethyl)-azepine Hydrochloride収率 71.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Stir a solution of 4-[2-(4-methanesulfonyl-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenol (160 mg, 0.39 mmol), 2-(hexamethyleneimino)-ethyl chloride hydrochloride (140 mg, 0.69 mmol), 60% sodium hydride (47 mg, 1.18 mmol) and N,N-dimethylformamide (2 mL) for 18 hours at ambient temperature, then evaporate under reduced pressure. Dissolve the residue in dichloromethane and wash with water, dry with solid magnesium sulfate and chromatograph on silica gel with dichloromethane/methanol mixtures. Combine the fractions containing product and add 1N hydrogen chloride in diethyl ether (0.30 mL). Concentrate the resulting solution under reduced pressure to give 160 mg of the title compound (69%). Mass spectrum (ion spray): m/z=546 (M+H).

後処理

  1. customevaporate under reduced pressure
  2. dissolutionDissolve the residue in dichloromethane
  3. washwash with water
  4. dry with materialdry with solid magnesium sulfate and chromatograph on silica gel with dichloromethane/methanol mixtures
  5. additionCombine the fractions containing product
  6. additionadd 1N hydrogen chloride in diethyl ether (0.30 mL)
  7. concentrationConcentrate the resulting solution under reduced pressure

出典と根拠

ORDレコード
ord-5e6451b196b345fdbd62d9e0a449de80
出典データセット
uspto-grants-2009_09
特許番号
US07585977B2

反応ノート

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