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Hydrochloric Acid → 4-(4-((4-Fluoroanilino)carbonyl)aminophenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxamide

HRID 387726
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HRID 387726 반응식
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][O:16][CH3:17])[N:9]=[CH:8][CH:7]=[C:6]2[O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[O:27])=[CH:21][CH:20]=1)#[N:2].[OH-:36].[Na+].Cl>CS(C)=O.O>[F:35][C:32]1[CH:31]=[CH:30][C:29]([NH:28][C:26]([NH:25][C:22]2[CH:21]=[CH:20][C:19]([O:18][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:3]([C:1]([NH2:2])=[O:36])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:24][CH:23]=2)=[O:27])=[CH:34][CH:33]=1
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10116220N-(4-(6-Cyano-7-(2-methoxyethoxy)-4-quinolyl)oxyphenyl)-N'-(4-fluorophenyl)urea

생성물 1

HCID 229369714-(4-((4-Fluoroanilino)carbonyl)aminophenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxamide수율 57.3%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매
HCID 962Water용매

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온도
80 °C

실험 절차

The N-(4-(6-cyano-7-(2-methoxyethoxy)-4-quinolyl)oxyphenyl)-N′-(4-fluorophenyl)urea (360 mg, 0.762 mmol) obtained in Example 10 was dissolved in dimethylsulfoxide (4.5 ml), and then 5N aqueous sodium hydroxide (1.5 ml) was added and the mixture was heated at 80° C. while stirring for 60 minutes. The reaction solution was cooled in an ice water bath, 2N hydrochloric acid (3.75 ml) was added for neutralization, and then the mixture was diluted with water (21 ml) and the precipitated crude crystals were filtered out. These were suspended in ethanol (20 ml) and subjected to sonication, and upon filtering out the crystals they were dried under reduced pressure to obtain the title compound (214 mg, 0.436 mmol, 57.3%) as gray crystals.

후처리

  1. temperatureThe reaction solution was cooled in an ice water bath
  2. customthe precipitated crude crystals
  3. filtrationwere filtered out
  4. customsubjected to sonication
  5. filtrationupon filtering out the crystals they
  6. customwere dried under reduced pressure

출처 및 근거

ORD 기록
ord-4a076820bbc74a548440b7756344f244
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08372981B2

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