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Triethylamine → N-methoxy-N-methyl-(E)-3-{2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl}propenamide

HRID 2380645
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HRID 2380645 반응식
CS(Cl)(=O)=O.[CH3:6][O:7][N:8]([CH3:34])[C:9](=[O:33])[CH2:10][CH:11]([C:13]1[C:14]([CH:30]2[CH2:32][CH2:31]2)=[N:15][C:16]2[C:21]([C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)O.C(N(CC)CC)C>ClCCl>[CH3:6][O:7][N:8]([CH3:34])[C:9](=[O:33])/[CH:10]=[CH:11]/[C:13]1[C:14]([CH:30]2[CH2:31][CH2:32]2)=[N:15][C:16]2[C:21]([C:22]=1[C:23]1[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2
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참가 물질

5

반응물 3

HCID 8471Triethylamine2회HCID 31297Methanesulfonyl chlorideHCID 18954750N-methoxy-N-methyl-3-{2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl}-3-hydroxypropanamide

생성물 1

HCID 22392020N-methoxy-N-methyl-(E)-3-{2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl}propenamide수율 80%

시약·촉매·용매 1

HCID 6344Dichloromethane
용매
2회

실험 절차

A dichloromethane (10 ml) solution of methanesulfonyl chloride (1.44 g, 12.6 mmol) was added to a dichloromethane (40 ml) solution of N-methoxy-N-methyl-3-{2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl}-3-hydroxypropanamide (3.30 g, 8.38 mmol) and triethylamine (1.27 g, 12.6 mmol). The resulting mixture was stirred at 0° C. for 30 minutes and at room temperature for 3 hours before treatment with triethylamine (1.27 g, 12.6 mmol). The mixture was heated to reflux for 3 hours, quenched with saturated NaHCO3 aq solution, and extracted with dichloromethane. The organic layer was washed with saturated NaCl aq solution, dried over magnesium sulfate, and then concentrated. The residue was purified by column chromatography (hexane:ethyl acetate=3:1) to give N-methoxy-N-methyl-(E)-3-{2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl}propenamide (2.52 g, 80% yield). mp=141° C. Rf =0.52 (hexane:ethyl acetate=2:1) IR (CHCl3): 3000, 1650, 1610, 1515, 1490, 1415, 1385, 1220, 1090, 1025, 840, 760 cm-1.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. customquenched with saturated NaHCO3 aq solution
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with saturated NaCl aq solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (hexane:ethyl acetate=3:1)

출처 및 근거

ORD 기록
ord-f50a223ce620460093676f43370b8c45
출처 데이터셋
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05369109

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