Pyridine → N-(6-(dibenzo[b,f]azocin-5(6H)-yl)-6-oxohexyl)trifluoroacetamide

HRID 1404654ノート

反応式

HRID 1404654 の反応式
[F:1][C:2]([F:15])([F:14])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](Cl)=[O:12])=[O:4].[CH:16]1[C:27]2[CH:26]=[CH:25][C:24]3[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=3[CH2:22][NH:21][C:20]=2[CH:19]=[CH:18][CH:17]=1.N1C=CC=CC=1>C(Cl)Cl>[CH:16]1[C:27]2[CH:26]=[CH:25][C:24]3[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=3[CH2:22][N:21]([C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:3](=[O:4])[C:2]([F:15])([F:14])[F:1])[C:20]=2[CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 114365186-(Trifluoroacetamido)hexanoyl chlorideHCID 66710187(Z)-5,6-dihydrodibenzo[b,f]azocine

生成物 1

HCID 86661634N-(6-(dibenzo[b,f]azocin-5(6H)-yl)-6-oxohexyl)trifluoroacetamide収率 71%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

6-(trifluoroacetamido)hexanoyl chloride (Clark et al., Chem. Soc. Perkin Trans. 1 2001:3312-3324) (0.984 g, 4.52 mmol) was added to a solution of 2 (0.75 g, 3.62 mmol) and pyridine (0.859 g, 10.86 mmol) in CH2Cl2 (approximately 10 ml) at room temperature, and stirred for 30 minutes. The reaction mixture was diluted with CH2Cl2 (approximately 20 mL), washed with water (2×30 mL), dried over anhydrous MgSO4 and the solvent was removed under reduced pressure. The residue was purified by chromatography (hexanes:ethyl acetate 2:3) to provide 1.064 g (2.56 mmol, 71%) of 3 as yellowish oil. 1H: δ 7.32-7.22 (m, 4H), 7.19-7.11 (m, 4H), 6.77 (d, J=13.2 Hz, 1H), 6.58 (d, J=13.2 Hz, 1H), 5.46 (d, J=14.8 Hz, 1H), 4.20 (d, J=14.8 Hz, 1H), 3.29-3.15 (m, 2H), 2.09-2.02 (m, 1H), 1.93-1.85 (m, 1H), 1.51-1.32 (m, 4H), 1.25-1.04 (m, 2H); 13C: 172.7, 157.5, 141.1, 136.1, 135.8, 134.8, 132.4, 131.8, 130.5, 128.5, 128.2, 128.1, 128.0, 127.3, 127.2, 117.5, 114.6, 54.8, 39.6, 34.3, 28.2, 25.9, 24.3; FIRMS (ESI+) m/z calcd for C23H24F3N2O2 [M+H]+ 417.1790. found 417.1783.

後処理

  1. washwashed with water (2×30 mL)
  2. dry with materialdried over anhydrous MgSO4
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by chromatography (hexanes:ethyl acetate 2:3)

出典と根拠

ORDレコード
ord-634c3be3f42646f1a5072d282483551a
出典データセット
uspto-grants-2014_12
特許番号
US08912322B2

反応ノート

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