Dimethyl Sulfoxide → HCID 86717887, Verbindung

HRID 2275775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2275775
[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 1A; 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 23A) were added. The reaction mixture was heated at reflux for 48 h and then concentrated under reduced pressure, 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, DMSO and water. The solid obtained was filtered off and dried under high vacuum. This gave 410 mg (15.4% of theory) of the title compound.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-7e50e0e2e4de4345a58b6cca89de105a
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09126998B2

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