1,1'-Carbonyldiimidazole → N-Methoxy-N-methyl-1H-indazole-3-carboxamide

HRID 218458

Reaktionsgleichung

Reaktionsgleichung von HRID 218458
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][N:5]=1)(O)=[O:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:26][NH:27][O:28][CH3:29]>CN(C=O)C>[CH3:29][O:28][N:27]([CH3:26])[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][N:5]=1)=[O:2]

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 78250Indazole-3-carboxylic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Produkt 1

HCID 16036867N-Methoxy-N-methyl-1H-indazole-3-carboxamideAusbeute 81,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

3-Carboxyindazole (10 g, 61.7 mmol) in DMF (100 mL) was treated with carbonyldiimidazole (11 g, 67.84 mmol) at rt with gas evolution for 15 min, after which the reaction mixture was heated up to 65° C. for 2 hours. After cooling to rt, N,O-dimethylhydroxyamine-HCl (4.14 g, 67.8 mmol) was added and the mixture was heated to 65° C. overnight. The reaction was cooled, quenched with water, extracted with CH2Cl2 and washed with water. The combined organic phase was dried and concentrated to afford N-methoxy-N-methyl-1H-indazole-3-carboxamide (10.3 g, 81.4%).

Aufarbeitung

  1. temperatureAfter cooling to rt
  2. temperaturethe mixture was heated to 65° C. overnight
  3. temperatureThe reaction was cooled
  4. customquenched with water
  5. extractionextracted with CH2Cl2
  6. washwashed with water
  7. customThe combined organic phase was dried
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c678d9ae3a624567bfad52efe9f10168
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198456B2

Verknüpfte Notizen

Wird geladen…