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

HRID 548503
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 548503
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 11430Potassium CarbonateHCID 685352-Butynoic acidHCID 216972946-Amino-4-(3-chloro-4-fluroanilino)-7-(4-methyl-1-piperazinyl)-3-quinolinecarbonitrile

Produkt 1

HCID 21697308N-[4-(3-Chloro-4-fluoroanilino)-3-cyano-7-(4-methyl-1-piperazinyl)-6-quinolinyl]-2-butynamideAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ae99d60588e744cd885418c2ea097940
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
USRE042376E1

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