Nitrogen → HCID 10114657, Verbindung

HRID 612222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 612222
ClC(OCC(C)C)=O.[CH3:9][N:10]([CH3:17])[CH2:11][C:12]#[C:13][C:14](O)=[O:15].CN1CCOCC1.N#N.[NH2:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[N:34]=[CH:33][C:32]([C:38]#[N:39])=[C:31]2[NH:40][C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([Br:47])[CH:42]=1>N1C=CC=CC=1>[Br:47][C:43]1[CH:42]=[C:41]([NH:40][C:31]2[C:30]3[C:35](=[CH:36][CH:37]=[C:28]([NH:27][C:14](=[O:15])[C:13]#[C:12][CH2:11][N:10]([CH3:17])[CH3:9])[CH:29]=3)[N:34]=[CH:33][C:32]=2[C:38]#[N:39])[CH:46]=[CH:45][CH:44]=1

Komponenten

7

Edukt 5

HCID 947NitrogenHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrileHCID 150797524-(Dimethylamino)but-2-ynoic acid

Produkt 1

HCID 10114657HCID 10114657, VerbindungAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Isobutyl chloroformate (0.342 g, 2.5 mmol) was dropwise added into an ice cold solution of 4-dimethylamino -2-butynoic acid (0.9 g, 3.8 mmol ) and N-methylmorpholine (0.384 g , 3.8 mmol ) in 50 mL of tetrahydrofuan under N2. After stirring for 30 min, a solution of 0.644 g (1.9 mmol ) of 6-amino-4-[(3-bromophenyl)amino]-3-quinolinecarbonitrile in 10 mL of pyridine was added dropwise and the mixture was stirred at 0° C. for 2.5 hr. The reaction was quenched with ice water, poured into saturated sodium bicarbonate and brine, and extracted with ethyl acetate. The ethyl acetate layer was concentrated and purified by thin-layer chromatography eluted with 15% methanol in ethyl acetate. The product was collected, and dried in vacuo to give 0.144 g (21%) of yellow solid; : mass spectrum (electrospray, m/e,): 447.9, 450.2 (M+H+); mp 180° C. (dec.).

Aufarbeitung

  1. stirringthe mixture was stirred at 0° C. for 2.5 hr
  2. customThe reaction was quenched with ice water
  3. additionpoured into saturated sodium bicarbonate and brine
  4. extractionextracted with ethyl acetate
  5. concentrationThe ethyl acetate layer was concentrated
  6. custompurified by thin-layer chromatography
  7. washeluted with 15% methanol in ethyl acetate
  8. customThe product was collected
  9. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6085ee38e6c04fb8a06a33f92b49694c
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06002008

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