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Sodium Iodide → 4-(3-Chloro-4-fluoro-phenylamino)-7-methoxy-6-pyrrolidin-1-yl-quinoline-3-carbonitrile

HRID 379194
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인쇄 미리보기

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HRID 379194 반응식
Cl[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[N:13]=[CH:12][C:11]([C:19]#[N:20])=[C:10]2[NH:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[C:24]([Cl:29])[CH:23]=1.N1CCOCC1.[I-].[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:29][C:24]1[CH:23]=[C:22]([NH:21][C:10]2[C:9]3[C:14](=[CH:15][C:16]([O:17][CH3:18])=[C:7]([N:6]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH:8]=3)[N:13]=[CH:12][C:11]=2[C:19]#[N:20])[CH:27]=[CH:26][C:25]=1[F:28]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 672046396-(4-Chlorobutylamino)-4-(3-chloro-4-fluorophenyamino)-7-methoxy-3-quinolinecarbonitrile

생성물 1

HCID 115674424-(3-Chloro-4-fluoro-phenylamino)-7-methoxy-6-pyrrolidin-1-yl-quinoline-3-carbonitrile

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
750 °C

실험 절차

A mixture of 2.5 g of 6-(4-chlorobutylamino)-4-(3-chloro-4-fluorophenyamino)-7-methoxy-3-quinolinecarbonitrile, 7.54 g of morpholine, and 0.17 g of sodium iodide in 30 ml of dimethylformamide was stirred at 750° C. for 7 hrs. The mixture was poured into dilute sodium bicarbonate and solid was collected. This material was dissolved in ethylacetate. The solution was dried over magnesium sulfate. The solvent was removed and the residue was chromatographed on silica gel using ethyl acetate-methanol-triethylamine mixtures. A more polar component (0.54 g) was 4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-6-(4-morpholin-4-yl-butylamino)-quinoline-3-carbonitrile; a less polar component (0.28 g) is the compound of this invention, 4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-6-pyrrolidin-1-yl-quinoline-3-carbonitrile, obtained as a yellow solid: mass spectrum electrospray, m/e): M+H 397.4.

후처리

  1. customwas collected
  2. dissolutionThis material was dissolved in ethylacetate
  3. dry with materialThe solution was dried over magnesium sulfate
  4. customThe solvent was removed
  5. customthe residue was chromatographed on silica gel
  6. customobtained as a yellow solid

출처 및 근거

ORD 기록
ord-3d7206cae7a041389d9e53f9bce32311
출처 데이터셋
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06297258B1

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