1,2-Dichloroethane → 4-[4-Chloro-3-(methyloxy)phenyl]-N-(3-ethyl-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide

HRID 734753Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734753
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH2:12])[CH:10]=2)[NH:5][N:4]=1)[CH3:2].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:25][C:24](=[O:26])[NH:23][C:22]([CH3:27])=[C:21]2[C:28](O)=[O:29])=[CH:16][C:15]=1[O:31][CH3:32].C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:25][C:24](=[O:26])[NH:23][C:22]([CH3:27])=[C:21]2[C:28]([NH:12][C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[NH:5][N:4]=[C:3]3[CH2:1][CH3:2])=[O:29])=[CH:16][C:15]=1[O:31][CH3:32]

Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 688272564-[4-Chloro-3-(methyloxy)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acidHCID 178438005HCID 178438005, Verbindung

Produkt 1

HCID 1784380114-[4-Chloro-3-(methyloxy)phenyl]-N-(3-ethyl-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamideAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

3-Ethyl-1H-indazol-5-amine (218 mg, 1.35 mmol, 1.00 equiv) was combined with the product from Example 93, Step 4 (0.400 g, 1.35 mmol, 1.00 equiv), EDC (0.310 g, 1.62 mmol, 1.2 equiv) and Et3N (226 μL, 1.62 mmol, 1.20 equiv) in DMF (4 mL) and stirred at 30° C. 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. Solid precipitated out of the organic phase and was filtered and triturated with ether to provide 295 mg (50%) of the title compound as a white solid. MS (ES+) m/e 439 [M+H]+

Aufarbeitung

  1. customThe phases were separated
  2. washthe organic phase was washed twice with 1N HCl, once with satd
  3. customSolid precipitated out of the organic phase
  4. filtrationwas filtered
  5. customtriturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-ae0e4c085be44ad5a6364f88fc28ea08
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592357B2

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