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1,2-Dichloroethane → 4-(4-Chlorophenyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide

HRID 734706
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 734706
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([OH:18])=O)=[CH:4][CH:3]=1.[NH2:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][C:28]=1[F:29])[NH:25][N:24]=[CH:23]2.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([NH:19][C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][C:28]=2[F:29])[NH:25][N:24]=[CH:23]3)=[O:18])=[CH:6][CH:7]=1
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Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 450905046-fluoro-1H-indazol-5-amineHCID 534357904-(4-Chlorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylic acid

Produkt 1

HCID 113954424-(4-Chlorophenyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamideAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The product of Example 4 Step 2 (240 mg, 0.903 mmol, 1.00 equiv), 5-amino-6-fluoroindazole (137 mg, 0.903 mmol, 1.0 equiv), and EDC (207 mg, 1.084 mmol, 1.20 equiv) were suspended in 2.0 mL DMF. Et3N (0.151 mL, 1.084 mmol, 1.2 equiv) was added and the solution was stirred at room temperature for 18 hrs. 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 (20-100% EtOAc in Hexanes) to provide 83 mg (23%) of the title compound as an off white solid. MS (ES+) m/e 399 [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 (20-100% EtOAc in Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-454d8a41455048559a1e486fc5cecd93
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07592357B2

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