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

HRID 734751Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734751
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[NH:4][N:3]=1.[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][C:14]=1[O:30][CH3:31].C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:27]([C:20]3[CH:19]([C:16]4[CH:17]=[CH:18][C:13]([Cl:12])=[C:14]([O:30][CH3:31])[CH:15]=4)[CH2:24][C:23](=[O:25])[NH:22][C:21]=3[CH3:26])=[O:28])[CH:9]=2)[NH:4][N:3]=1

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 178507356HCID 178507356, Verbindung

Produkt 1

HCID 178487580N-(3-Bromo-1H-indazol-5-yl)-4-[4-chloro-3-(methyloxy)phenyl]-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-Bromo-1H-indazol-5-amine (126 mg, 0.592 mmol, 1.00 equiv) was combined with the product from Example 93, Step 4 (175 mg, 0.592 mmol, 1.00 equiv), EDC (134 mg, 0.710 mmol, 1.20 equiv) and Et3N (99 μL, 0.710 mmol, 1.20 equiv) in DMF (1.75 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 145 mg (50%) of the title compound as a white solid. MS (ES+) m/e 490 [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-111992cf1c2c40fa93d9573539876475
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592357B2

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