Dimethyl Sulfoxide → 6-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-pyridin-3-ol

HRID 533925

Reaktionsgleichung

Reaktionsgleichung von HRID 533925
CS(C)=O.[OH:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([OH:14])=O)=[N:10][CH:11]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.O[NH:28][C:29](=[NH:33])[CH:30]([CH3:32])[CH3:31]>CC(=O)OCC>[CH:30]([C:29]1[N:33]=[C:12]([C:9]2[N:10]=[CH:11][C:6]([OH:5])=[CH:7][CH:8]=2)[O:14][N:28]=1)([CH3:32])[CH3:31]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 682631,1'-CarbonyldiimidazoleHCID 2687405-Hydroxypyridine-2-carboxylic acidHCID 178449908HCID 178449908, Verbindung

Produkt 1

HCID 1363773006-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-pyridin-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To DMSO (25 mL) was added 5-hydroxy-pyridine-2-carboxylic acid (1.0 g) and CDI (1.3 g). After 15 minutes N-hydroxy-isobutyramidine (820 mg) was added. After 1 hour the mixture was heated to 90° C. for 1 hour. After the mixture reached room temperature, it was diluted with EA and washed three times with HCl (0.1 M). The organic phase was dried (Na2SO4) and concentrated to provide the title compound. MS ESI+: m/z=206 [M+H]+.

Aufarbeitung

  1. customreached room temperature
  2. washwashed three times with HCl (0.1 M)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-989f920584734f61b7577085f4131722
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853412B2

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