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Dicyclohexylcarbodiimide → N-[4-(3-Chloro-4-fluoroanilino)-3-cyano-7-(4-methyl-1-piperazinyl)-6-quinolinyl]-2-butynamide

HRID 548503
ノート
印刷プレビュー

反応式

HRID 548503 の反応式
[C:1]([OH:6])(=O)[C:2]#[C:3][CH3:4].C1CCC(N=C=NC2CCCCC2)CC1.[NH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][C:32]=1[N:33]1[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]1)[N:29]=[CH:28][C:27]([C:40]#[N:41])=[C:26]2[NH:42][C:43]1[CH:48]=[CH:47][C:46]([F:49])=[C:45]([Cl:50])[CH:44]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[Cl:50][C:45]1[CH:44]=[C:43]([CH:48]=[CH:47][C:46]=1[F:49])[NH:42][C:26]1[C:25]2[C:30](=[CH:31][C:32]([N:33]3[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]3)=[C:23]([NH:22][C:1](=[O:6])[C:2]#[C:3][CH3:4])[CH:24]=2)[N:29]=[CH:28][C:27]=1[C:40]#[N:41]
参加物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 10868DicyclohexylcarbodiimideHCID 11430Potassium CarbonateHCID 685352-Butynoic acidHCID 216972946-Amino-4-(3-chloro-4-fluroanilino)-7-(4-methyl-1-piperazinyl)-3-quinolinecarbonitrile

生成物 1

HCID 21697308N-[4-(3-Chloro-4-fluoroanilino)-3-cyano-7-(4-methyl-1-piperazinyl)-6-quinolinyl]-2-butynamide収率 69.2%

試薬・触媒・溶媒

1
HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred solution of 2-butynoic acid (0.25 g, 3.0 mmol) in 1.5 ml of DCM at 0° was added DCC (0.21 g, 1.0 mmol). After 15 m the mixture was warmed to 25°, recooled to 0°, and treated with 6-amino-4-(3-chloro-4-fluroanilino)-7-(4-methyl-1-piperazinyl)-3-quinolinecarbonitrile (0.21 g, 0.50 mmol) followed by 0.5 ml DCM rinse. The resulting mixture was stirred at 25° for 18 h and filtered to remove dicyclohexyl urea. The filtrate was partitioned with water which contained potassium carbonate (0.4 g, 3 mmol). The organic layer was washed with water, dried, and concentrated. The residue was passed as a solution in DCM onto a pad of silica gel. The product was eluted with 50:2:1 acetone-MeOH-TEA and concentrated to give 0.165 g amorphous solid; ms 477.2 (M+H)+, 239.1 (M+2H)+2.

後処理

  1. temperatureAfter 15 m the mixture was warmed to 25°
  2. customrecooled to 0°
  3. washrinse
  4. filtrationfiltered
  5. customto remove dicyclohexyl urea
  6. customThe filtrate was partitioned with water which
  7. washThe organic layer was washed with water
  8. customdried
  9. concentrationconcentrated
  10. washThe product was eluted with 50:2:1 acetone-MeOH-TEA
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-ae99d60588e744cd885418c2ea097940
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

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