1,2-Dichloroethane → Dihydropyridone indazole amide 10

HRID 734671Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734671
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][C:13](=[O:15])[NH:12][C:11]([CH3:16])=[C:10]2[C:17](O)=[O:18])=[CH:5][CH:4]=1.[NH:22]1[C:30]2[C:25](=[CH:26][C:27]([NH2:31])=[CH:28][CH:29]=2)[CH:24]=[N:23]1.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[NH:22]1[C:30]2[C:25](=[CH:26][C:27]([NH:31][C:17]([C:10]3[CH:9]([C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:20])([F:21])[F:1])=[CH:8][CH:7]=4)[CH2:14][C:13](=[O:15])[NH:12][C:11]=3[CH3:16])=[O:18])=[CH:28][CH:29]=2)[CH:24]=[N:23]1

Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 880121H-Indazol-5-amineHCID 160998632-Methyl-6-oxo-4-(4-(trifluoromethyl)phenyl)-1,4,5,6-tetrahydropyridine-3-carboxylic acid

Produkt 1

HCID 11189172Dihydropyridone indazole amide 10Ausbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The product of step 2 (146 mg, 0.512 mmol, 1.00 equiv), 1H-indazol-5-amine (68 mg, 0.512 mmol, 1.00 equiv) and EDC (118 mg, 0.615 mmol, 1.20 equiv) were suspended in 8.0 mL DMF. Et3N (0.086 mL, 0.615 mmol, 1.20 equiv) was added and the solution was stirred overnight at room temperature. The reaction mixture was diluted with EtOAc and 1N HCl. The phases were separated, and the organic phase was washed twice with 1N HCl, once with satd. NaHCO3, and once with satd. NaCl. The organic phase was dried over Na2SO4, filtered, and concentrated en vacuo. The residue was purified by flash chromatography (100% EtOAc) to provide 0.070 g (33%) of the title compound as a white solid. MS (ES+) m/e 415 [M+H]+

Aufarbeitung

  1. customThe phases were separated
  2. washthe organic phase was washed twice with 1N HCl, once with satd
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated en vacuo
  6. customThe residue was purified by flash chromatography (100% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-b01322396f4d493bab760eb89b7f6196
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592357B2

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