Sodium Iodide → N-{2-[ethyl(2-hydroxyethyl)amino]ethyl}-3-methoxy-N-methyl-4-oxo-5-(2-oxo-2-phenylethyl)-4,5-dihydrothieno[3,2-c]quinoline-2-carboxamide

HRID 1947131ノート

反応式

HRID 1947131 の反応式
Cl[CH2:2][CH2:3][N:4]([CH3:32])[C:5]([C:7]1[S:19][C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]([CH2:20][C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:10](=[O:29])[C:9]=2[C:8]=1[O:30][CH3:31])=[O:6].C(NC([OH:38])C)C.[CH:39]([N:42](C(C)C)[CH2:43][CH3:44])(C)[CH3:40].[I-].[Na+]>C(O)CCC.C(=O)([O-])O.[Na+]>[CH2:39]([N:42]([CH2:43][CH2:44][OH:38])[CH2:2][CH2:3][N:4]([CH3:32])[C:5]([C:7]1[S:19][C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]([CH2:20][C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:10](=[O:29])[C:9]=2[C:8]=1[O:30][CH3:31])=[O:6])[CH3:40]

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 18179409EthylaminoethanolHCID 66893214N-(2-chloroethyl)-3-methoxy-N-methyl-4-oxo-5-(2-oxo-2-phenylethyl)-4,5-dihydrothieno[3,2-c]quinoline-2-carboxamide

生成物 1

HCID 57860044N-{2-[ethyl(2-hydroxyethyl)amino]ethyl}-3-methoxy-N-methyl-4-oxo-5-(2-oxo-2-phenylethyl)-4,5-dihydrothieno[3,2-c]quinoline-2-carboxamide収率 35.7%

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

A solution of the obtained N-(2-chloroethyl)-3-methoxy-N-methyl-4-oxo-5-(2-oxo-2-phenylethyl)-4,5-dihydrothieno[3,2-c]quinoline-2-carboxamide (200 mg, 0.43 mmol), N-ethylaminoethanol (228 mg, 2.55 mmol), diisopropylethylamine (330 mg, 2.55 mmol) and sodium iodide (64 mg, 0.43 mmol) in 1-butanol (5 mL) was stirred at 110° C. for 18 hr. The reaction mixture was diluted with saturated sodium hydrogen carbonate solution, and extracted twice with ethyl acetate. The extract was combined, washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate to ethyl acetate/methanol=20/1) to give N-{2-[ethyl(2-hydroxyethyl)amino]ethyl}-3-methoxy-N-methyl-4-oxo-5-(2-oxo-2-phenylethyl)-4,5-dihydrothieno[3,2-c]quinoline-2-carboxamide (0.08 g) as a white non-crystalline solid.

後処理

  1. extractionextracted twice with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by aminosilica gel chromatography (eluate; ethyl acetate to ethyl acetate/methanol=20/1)

出典と根拠

ORDレコード
ord-d0b7c70b85434e81a27e4d0ccaf93e95
出典データセット
uspto-grants-2013_03
特許番号
US08399449B2

反応ノート

読み込み中…