Dimethylformamide → {N-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-N-(pyridin-4-ylmethyl)carbamoyloxy}acetic acid ethyl ester

HRID 1504192노트

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HRID 1504192 반응식
[C:1](=[O:4])([O-:3])[O-].[K+].[K+].CN(C=O)C.[CH3:12][N:13]1[C:22]2[C:17](=[CH:18][C:19]([O:23][CH2:24][CH2:25][CH2:26][NH:27][CH2:28][C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]1=[O:35].Br[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39]>C(OCC)(=O)C>[CH2:41]([O:40][C:38](=[O:39])[CH2:37][O:3][C:1](=[O:4])[N:27]([CH2:26][CH2:25][CH2:24][O:23][C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[N:13]([CH3:12])[C:14](=[O:35])[CH:15]=[CH:16]2)[CH2:28][C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1)[CH3:42]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 86762689HCID 86762689, 화합물

생성물 1

HCID 90369233{N-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-N-(pyridin-4-ylmethyl)carbamoyloxy}acetic acid ethyl ester

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

Potassium carbonate (1.66 g) was added to a DMF solution (50 ml) of 1-methyl-6-{3-[(pyridin-4-ylmethyl)amino]propoxy}-1H-quinolin-2-one (1.5 g). The mixture was cooled to 0° C., and ethyl bromoacetate (1.16 ml) was added to the mixture and stirred at room temperature overnight. The reaction mixture was added to ice water, and extraction with ethyl acetate was performed. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate: methanol=20:1→10:1). The purified product was condensed under reduced pressure. The residue was recrystallized from ether, and dried to give the title compound(0.55 g) as a white powder.

후처리

  1. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate: methanol=20:1→10:1)
  5. customcondensed under reduced pressure
  6. customThe residue was recrystallized from ether
  7. customdried

출처 및 근거

ORD 기록
ord-a63a4b0c5de44a9b9dfd9d1e2b7cee0e
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212187B2

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