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

HRID 548497
ノート
印刷プレビュー

反応式

HRID 548497 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
750 °C

実験手順

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-l-yl-quinoline-3-carbonitrile, obtained as a yellow solid: mass spectrum electrospray, m/e): M+H 397.4.

後処理

  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

出典と根拠

ORDレコード
ord-842040b65cd84c428fc1f4003781e0ae
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
USRE042376E1

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート