Hydrochloric Acid → HCID 23125711, Verbindung

HRID 1820917

Reaktionsgleichung

Reaktionsgleichung von HRID 1820917
[C:1]([O:9][CH3:10])(=[O:8])[CH2:2][CH2:3][CH2:4][C:5]([O-:7])=O.S(Cl)(Cl)=O.[NH2:15][C:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[O:18][C:17]=1[C:25]([NH:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][N:29]=1)=[O:26].Cl>C(Cl)(Cl)Cl.CN(C)C=O.N1C=CC=CC=1>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([NH:27][C:25]([C:17]2[O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:16]=2[NH:15][C:5](=[O:7])[CH2:4][CH2:3][CH2:2][C:1]([O:9][CH3:10])=[O:8])=[O:26])=[N:29][CH:30]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 69931945-Methoxy-5-oxopentanoateHCID 23062590HCID 23062590, Verbindung

Produkt 1

HCID 23125711HCID 23125711, VerbindungAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 1049PyridineLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Monomethyl glutarate (3.32 g) is dissolved in chloroform (50 ml) and thereto are added thionyl chloride (1.75 ml) and N,N-dimethylformamide (one drop). After stirring for 1.5 hours at the same temperature, the reaction solution is cooled, and thereto are added 3-amino-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (5.00 g) obtained in Reference Example 80 and pyridine (7.0 ml). After stirring for 2.5 hours at room temperature, the reaction solution is poured into 5% hydrochloric acid and extracted with chloroform. The organic layer is washed successively with saturated brine, a saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, and evaporated to remove the solvent under reduced pressure. The resulting residue is suspended in diisopropyl ether and the precipitates are collected by filtration to give methyl 5-[(2-{[(5-chloropyridin-2-yl)amino]carbonyl}benzofuran-3-yl)amino]-5-oxopentanoate (6.16 g). APCI-MS M/Z:416/418[M+H]+

Aufarbeitung

  1. temperaturethe reaction solution is cooled
  2. stirringAfter stirring for 2.5 hours at room temperature
  3. extractionextracted with chloroform
  4. washThe organic layer is washed successively with saturated brine
  5. dry with materiala saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate
  6. customevaporated
  7. customto remove the solvent under reduced pressure
  8. filtrationthe precipitates are collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-c3542a4506fc4137b0d2af184aa3883b
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07605158B2

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