Dimethyl Sulfoxide → HCID 86717887, Verbindung

HRID 1624081Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1624081
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][CH:11]=1.Cl[CH:19]([C:25]([CH:27]1[CH2:29][CH2:28]1)=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21].CS(C)=O.O>C(O)C.CO>[CH:27]1([C:25]2[N:12]=[C:7]3[C:6]([O:5][CH2:4][C:3]4[C:13]([F:17])=[CH:14][CH:15]=[CH:16][C:2]=4[F:1])=[CH:11][CH:10]=[CH:9][N:8]3[C:19]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:29][CH2:28]1

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 102634983-(2,6-Difluoro-benzyloxy)-pyridin-2-ylamineHCID 54244501Ethyl 2-chloro-3-cyclopropyl-3-oxopropanoate2×

Produkt 1

HCID 86717887HCID 86717887, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

1.69 g of 3-[(2,6-difluorobenzyl)oxy]pyridine-2-amine (Example 4A; 7.13 mmol, 1 equivalent) were initially charged in 44.4 ml of ethanol, and 425 mg of powdered molecular sieve 3 Å and 6.8 g of ethyl 2-chloro-3-cyclopropyl-3-oxopropanoate (crude product from Example 26A) were added. The resulting reaction mixture was heated at reflux for 48 h and then concentrated, and the residue was chromatographed (cyclohexane/ethyl acetate as mobile phase). The product-containing fractions were combined and concentrated under reduced pressure. The residue obtained in this manner was taken up in methanol, dimethyl sulphoxide and water and the solid formed was filtered off and dried under high vacuum. This gave 410 mg (15.4% of theory) of the title compound.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 48 h
  4. concentrationconcentrated
  5. customthe residue was chromatographed (cyclohexane/ethyl acetate as mobile phase)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained in this manner
  8. filtrationwas filtered off
  9. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-98a7c69d78ec4b4b9e8a95a8ffdb69ba
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778964B2

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