Potassium Iodide → 4-(6-Cyano-7-(3-(4-pyridyl)propoxy)-4-quinolyl)oxyphenyl-N'-(4-methoxyphenyl)urea

HRID 387700

반응식

HRID 387700 반응식
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O-:13])[N:9]=[CH:8][CH:7]=[C:6]2[O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[O:23])=[CH:17][CH:16]=1)#[N:2].[Na+].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:43][CH2:44][CH2:45][C:46]1[CH:51]=[CH:50][N:49]=[CH:48][CH:47]=1>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:43][CH2:44][CH2:45][C:46]1[CH:51]=[CH:50][N:49]=[CH:48][CH:47]=1)[N:9]=[CH:8][CH:7]=[C:6]2[O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)=[O:23])=[CH:17][CH:16]=1)#[N:2]

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2054424-(3-Chloropropyl)pyridineHCID 23711333Sodium 6-cyano-4-(4-((4-methoxyanilino)carbonyl)aminophenoxy)-7-quinolinolate

생성물 1

HCID 101659374-(6-Cyano-7-(3-(4-pyridyl)propoxy)-4-quinolyl)oxyphenyl-N'-(4-methoxyphenyl)urea수율 24.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

The sodium 6-cyano-4-(4-((4-methoxyanilino)carbonyl)aminophenoxy)-7-quinolinolate (200 mg) synthesized in Example 87 was dissolved in dimethylformamide (4 ml), and then potassium carbonate (130 mg, 0.9400 mmol), potassium iodide (3 mg) and 1-chloro-3-(4-pyridyl)propane (80 mg, 0.5159 mmol) were added and the mixture was heated and stirred at 80° C. for 5 hours and 30 minutes. After allowing the mixture to stand and adding saturated saline, it was extracted with ethyl acetate, washed with saturated saline and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate-methanol system). The obtained crystals were suspended in ethanol, the suspension was diluted with diethyl ether, and the crystals were filtered out, washed with diethyl ether and dried by aspiration to obtain the title compound (60 mg) as light yellow crystals.

후처리

  1. temperaturethe mixture was heated
  2. additionadding saturated saline, it
  3. extractionwas extracted with ethyl acetate
  4. washwashed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was purified by NH silica gel column chromatography (ethyl acetate-methanol system)
  8. additionthe suspension was diluted with diethyl ether
  9. filtrationthe crystals were filtered out
  10. washwashed with diethyl ether
  11. customdried by aspiration

출처 및 근거

ORD 기록
ord-9d10ecd3780c4978bb8dccfda15a9c1c
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372981B2

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