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

HRID 2380645
ノート
印刷プレビュー

反応式

HRID 2380645 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471Triethylamine2 回HCID 31297Methanesulfonyl chlorideHCID 18954750N-methoxy-N-methyl-3-{2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl}-3-hydroxypropanamide

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒
2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f50a223ce620460093676f43370b8c45
出典データセット
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05369109

反応ノート

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