Sodium Carbonate → 4-(1H-indazol-6-ylamino)-5,8-dimethoxy-quinoline-3-carbonitrile

HRID 1595788Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1595788
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[CH:9][C:10]=2[O:12][CH3:13])[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[NH2:18][C:19]1[CH:27]=[C:26]2[C:22]([CH:23]=[N:24][NH:25]2)=[CH:21][CH:20]=1.C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[NH:25]1[C:26]2[C:22](=[CH:21][CH:20]=[C:19]([NH:18][C:2]3[C:11]4[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[CH:9][C:10]=4[O:12][CH3:13])[N:5]=[CH:4][C:3]=3[C:16]#[N:17])[CH:27]=2)[CH:23]=[N:24]1

Komponenten

6

Edukt 4

HCID 10340Sodium CarbonateHCID 814231H-Indazol-6-amineHCID 101298981-EthoxyethanolHCID 224665354-Chloro-5,8-dimethoxyquinoline-3-carbonitrile

Produkt 1

HCID 217047734-(1H-indazol-6-ylamino)-5,8-dimethoxy-quinoline-3-carbonitrileAusbeute 91,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 0.148 g of 4-chloro-5,8-dimethoxy-quinolin-3-carbonitrile, 0.093 g of 6-aminoindazole, and 5 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 30 minutes. The mixture was cooled and added to 50 ml of water. To this mixture was added sodium carbonate to pH 9. The product was collected, washed with water, dried, and washed with 10 ml of hexanes-ethyl acetate (4:1) to give 0.189 g of 4-(1H-indazol-6-ylamino)-5,8-dimethoxy-quinoline-3-carbonitrile as a solid, mp 302-305° C.; mass spectrum (EI, m/e): M 345.1223.

Aufarbeitung

  1. temperatureat reflux temperature for 30 minutes
  2. temperatureThe mixture was cooled
  3. customThe product was collected
  4. washwashed with water
  5. customdried
  6. washwashed with 10 ml of hexanes-ethyl acetate (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-197f7986dc684fd4bb0b3c266fa20a62
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06288082B1

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