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

HRID 734721
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 734721
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[NH2:11].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:24][C:23](=[O:25])[NH:22][C:21]([CH3:26])=[C:20]2[C:27](O)=[O:28])=[CH:15][CH:14]=1.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[NH:11][C:27]([C:20]1[CH:19]([C:16]2[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=2)[CH2:24][C:23](=[O:25])[NH:22][C:21]=1[CH3:26])=[O:28]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 220224116-Chloro-1H-indazol-5-amineHCID 534357904-(4-Chlorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylic acid

Produkt 1

HCID 11750349N-(6-Chloro-1H-indazol-5-yl)-4-(4-chlorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamideAusbeute 25,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

6-Chloro-1H-indazol-5-amine (64 mg, 0.382 mmol, 1.0 equiv) was combined with the product from Example 4, Step 2 (101 mg, 0.382 mmol, 1.0 equiv), EDC (88 mg, 0.458 mmol, 1.2 equiv) and Et3N (64 μL, 0.458 mmol, 1.2 equiv) in DMF (1 mL) and stirred at room temperature for 18 hours. 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 concentrated en vacuo. The residue was purified by flash chromatography (0-100% EtOAc in Hexanes) and further purified by reverse-phase HPLC (15-98% CH3CN/H2O, adjusted to pH 10 w/NH4OH over 13 minutes, retention time 6.56 min) to provide 40 mg (25%) of the title compound as a white solid. MS (ES+) m/e 416 [M+H]+

Aufarbeitung

  1. customThe phases were separated
  2. washthe organic phase was washed twice with 1N HCl, once with satd
  3. concentrationThe organic phase was concentrated en vacuo
  4. customThe residue was purified by flash chromatography (0-100% EtOAc in Hexanes)
  5. customfurther purified by reverse-phase HPLC (15-98% CH3CN/H2O, adjusted to pH 10 w/NH4OH over 13 minutes, retention time 6.56 min)

Quellen und Nachweise

ORD-Eintrag
ord-a95754020c534033bdc1903f0198c278
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07592357B2

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