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

HRID 1404654노트

반응식

HRID 1404654 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-634c3be3f42646f1a5072d282483551a
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912322B2

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