1-Bromo-2-Chloroethane → N-(4-(6-Cyano-7-(2-chloroethoxy)-4-quinolyl)oxyphenyl)-N'-(4-fluorophenyl)urea

HRID 853244노트

반응식

HRID 853244 반응식
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH: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]([F:31])=[CH:27][CH:26]=2)=[O:23])=[CH:17][CH:16]=1)#[N:2].Br[CH2:33][CH2:34][Cl:35].C(=O)([O-])[O-].[K+].[K+].O1CCCC1>CN(C)C=O.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:33][CH2:34][Cl:35])[N:9]=[CH:8][CH:7]=[C:6]2[O:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22]([NH:24][C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)=[O:23])=[CH:19][CH:20]=1)#[N:2]

참가 물질

7

반응물 4

HCID 78491-Bromo-2-ChloroethaneHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 135829395N-(4-(6-Cyano-7-hydroxy-4-quinolyl)oxyphenyl)-N'-(4-fluorophenyl)urea

생성물 1

HCID 22936803N-(4-(6-Cyano-7-(2-chloroethoxy)-4-quinolyl)oxyphenyl)-N'-(4-fluorophenyl)urea수율 75.72%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
55 °C

실험 절차

N-(4-(6-Cyano-7-hydroxy-4-quinolyl)oxyphenyl)-N′-(4-fluorophenyl)urea (400 mg, 0.9166 mmol) was dissolved in dimethylformamide (5.0 ml), and then 1-bromo-2-chloroethane (0.12 ml, 1.4479 mmol) and potassium carbonate (200 mg, 1.4479 mmol) were added and the mixture was heated and stirred at 55° C. for 4 hours. After cooling, tetrahydrofuran and ethyl acetate were added, the mixture was washed with saturated brine and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to NH silica gel column chromatography (ethyl acetate-methanol system). The obtained crystals were suspended in diethyl ether, the suspension was diluted with hexane, and the crystals were filtered out, washed with hexane and dried by aspiration to obtain the title compound (331 mg, 0.6941 mmol, 75.72%) as light yellow crystals.

후처리

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling
  3. washthe mixture was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionthe suspension was diluted with hexane
  7. filtrationthe crystals were filtered out
  8. washwashed with hexane
  9. customdried by aspiration

출처 및 근거

ORD 기록
ord-a680a3d0db04466a8e64b5829b28c12e
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253286B2

반응 노트

불러오는 중…