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

HRID 734665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734665
[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)=[C:4]([F:19])[CH:3]=1.[NH:20]1[C:28]2[C:23](=[CH:24][C:25]([NH2:29])=[CH:26][CH:27]=2)[CH:22]=[N:21]1.C(Cl)CCl.CCN(CC)CC>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOC(C)=O.Cl>[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]([NH:29][C:25]2[CH:24]=[C:23]3[C:28](=[CH:27][CH:26]=2)[NH:20][N:21]=[CH:22]3)=[O:18])=[C:4]([F:19])[CH:3]=1

Komponenten

9

Edukt 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 880121H-Indazol-5-amineHCID 688260574-(4-Chloro-2-fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid

Produkt 1

HCID 112809884-(4-Chloro-2-fluorophenyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamideAusbeute 28,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The product of step 2 (252 mg, 0.890 mmol, 1.00 equiv), 1H-indazol-5-amine (142 mg, 1.07 mmol, 1.20 equiv), EDC (229 mg, 1.07 mmol, 1.20 equiv), and DMAP (10 mg, catalytic) were suspended in 4.0 mL DMF. Et3N (0.298 mL, 2.14 mmol, 1.00 equiv) was added and the solution was heated to 80° C. for 2 hours. The reaction mixture was cooled to room temperature and 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 0.100 g (28%) of the title compound as a white solid. MS (ES+) m/e 399 [M+H]+

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-2e5a45b2487249ee9e7d5fccb481e407
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592357B2

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