1,2-Dichloroethane → N-methoxy-N-methyl-1H-indazole-5-carboxamide

HRID 240756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 240756
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[CH3:13][NH:14][O:15][CH3:16].C(N(CC)CC)C.C(Cl)CCl>ClCCl.CN(C)C=O>[CH3:16][O:15][N:14]([CH3:13])[C:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][N:2]=[CH:3]2)=[O:12]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 42484541H-Indazole-5-carboxylic acid

Produkt 1

HCID 62814299N-methoxy-N-methyl-1H-indazole-5-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of Example 75A (1.6 g, 10 mmol) and N,O-dimethylhydroxylamine (1.1 g, 11 mmol) in dichloromethane (40 mL) and dimethylformamide (10 mL) was added triethylamine (1.67 mL, 12 mmol) and EDC (2.1 g, 11 mmol), and the mixture was stirred at room temperature for 24 hours. The solvents were evaporated under reduced pressure, and the resulting residue was diluted with ethyl acetate and washed with water. The organic layer was dried over sodium sulfate and purified by silica gel column chromatography in ethyl acetate to afford the title compound. MS (ESI+) m/z 206.0 (M+H)+.

Aufarbeitung

  1. customThe solvents were evaporated under reduced pressure
  2. additionthe resulting residue was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. custompurified by silica gel column chromatography in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-81dfba45d17644a79ebb861f7e26b292
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648069B2

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