N,N-Dimethylethylenediamine → 6-(((dimethylamino)ethyl)amino)-3-fluoro-7H-indeno[2,1-c]quinoline-7-on dihydrochloride

HRID 3155

반응식

HRID 3155 반응식
[Cl:1][C:2]1[C:11]2[C:12](=[O:19])[C:13]3[C:18]([C:10]=2[C:9]2[C:4](=[CH:5][C:6]([F:20])=[CH:7][CH:8]=2)[N:3]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3.[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH2:25]>>[ClH:1].[ClH:1].[CH3:21][N:22]([CH2:23][CH2:24][NH:25][C:2]1[C:11]2[C:12](=[O:19])[C:13]3[C:18]([C:10]=2[C:9]2[C:4](=[CH:5][C:6]([F:20])=[CH:7][CH:8]=2)[N:3]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH3:26]

참가 물질

3

반응물 2

HCID 66053N,N-DimethylethylenediamineHCID 193561006-chloro-3-fluoro-7H-indeno[2,1-c]quinoline-7-on

생성물 1

HCID 193561156-(((dimethylamino)ethyl)amino)-3-fluoro-7H-indeno[2,1-c]quinoline-7-on dihydrochloride수율 68.6%

반응 조건

온도
90 °C

실험 절차

To a suspension of 6-chloro-3-fluoro-7H-indeno[2,1-c]quinoline-7-on (860 mg, 3.0 mmol) in pyrydine (10 ml) was added N,N-dimethylethylenediamine (800 mg, 9.0 mmol), and the mixture was stirred with heat at 90° C. for 12 hours. The reaction mixture was distilled to dryness. To the residue was added water and chloroform for extraction. The chloroform layer was dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (eluent; chloroform:ethanol=10:1(v/v)). The purified material was dissolved in 20 ml of tetrahydrofuran. To the the solution was added 4N-hydrochloride/dioxane (2 ml) and the mixture was concentrated under reduced pressure. The residue obtained was crystallized from diethylether to give 420 mg (yield 34.3%) of title compound. The physicochemical properties thereof are shown in table 1.

후처리

  1. distillationThe reaction mixture was distilled to dryness
  2. additionTo the residue was added water and chloroform
  3. extractionfor extraction
  4. dry with materialThe chloroform layer was dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (eluent; chloroform:ethanol=10:1(v/v))
  7. dissolutionThe purified material was dissolved in 20 ml of tetrahydrofuran
  8. additionTo the the solution was added 4N-hydrochloride/dioxane (2 ml)
  9. concentrationthe mixture was concentrated under reduced pressure
  10. customThe residue obtained
  11. customwas crystallized from diethylether

출처 및 근거

ORD 기록
ord-afb2bac37106446f80150be5390395af
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733918

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