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 1513585

반응식

HRID 1513585 반응식
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]

참가 물질

7

반응물 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

생성물 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-carboxamide수율 35.7%

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f7b9261f25ba4548b4aaa785df93ba50
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217176B2

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