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Pyridine → HCID 59717043, Verbindung

HRID 75633
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 75633
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13]3[N:14]([CH3:30])[C:15](=[O:29])[CH:16]=[C:17]([O:18][S:19]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[C:12]=3[C:11](=[O:31])[N:10]([CH:32]3[CH2:34][CH2:33]3)[C:9]2=[O:35])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>C(Cl)(Cl)Cl>[CH:32]1([N:10]2[C:11](=[O:31])[C:12]3[C:17]([O:18][S:19]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)(=[O:21])=[O:20])=[CH:16][C:15](=[O:29])[N:14]([CH3:30])[C:13]=3[N:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][S:43]([CH3:42])(=[O:45])=[O:44])[CH:3]=3)[C:9]2=[O:35])[CH2:33][CH2:34]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 59717362HCID 59717362, Verbindung

Produkt 1

HCID 59717043HCID 59717043, VerbindungAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To toluene-4-sulfonic acid 1-(3-aminophenyl)-3-cyclopropyl-8-methyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester 13 (5 g) obtained in Step 7 was added pyridine (40 ml), a solution of methanesulfonyl chloride 14 (0.9 ml) in chloroform (10 ml) was added dropwise with stirring under ice-cooling, and the mixture was stirred for 3 hrs in an ice bath. The reaction mixture was concentrated under reduced pressure, 2N hydrochloric acid was added and the mixture was extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resultant solid was suspended in diethyl ether:hexane=1:1, and filtered by suction to give toluene-4-sulfonic acid 3-cyclopropyl-1-(3-methanesulfonylaminophenyl)-8-methyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester (5.5 g, 95%) as a white solid.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred for 3 hrs in an ice bath
  3. concentrationThe reaction mixture was concentrated under reduced pressure, 2N hydrochloric acid
  4. additionwas added
  5. extractionthe mixture was extracted with chloroform
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. filtrationhexane=1:1, and filtered by suction

Quellen und Nachweise

ORD-Eintrag
ord-e06c83e928454475b3d5469954384532
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08835443B2

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