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1,2-Dichloroethane → 4-(4-Chloro-2-fluorophenyl)-2-methyl-N-(7-methyl-1H-indazol-5-yl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide

HRID 734696
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 734696
[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.[NH2:20][C:21]1[CH:22]=[C:23]2[C:27](=[C:28]([CH3:30])[CH:29]=1)[NH:26][N:25]=[CH:24]2.C(Cl)CCl.CCN(CC)CC>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:20][C:21]2[CH:22]=[C:23]3[C:27](=[C:28]([CH3:30])[CH:29]=2)[NH:26][N:25]=[CH:24]3)=[O:18])=[C:4]([F:19])[CH:3]=1
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Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 13820227-methyl-1H-indazol-5-amineHCID 688260574-(4-Chloro-2-fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid

Produkt 1

HCID 112928534-(4-Chloro-2-fluorophenyl)-2-methyl-N-(7-methyl-1H-indazol-5-yl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamideAusbeute 26,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The product of Example 3 Step 2 (180 mg, 0.635 mmol, 1.00 equiv), 5-amino-7-methylindazole (94 mg, 0.635 mmol, 1.0 equiv), and EDC (145 mg, 0.761 mmol, 1.20 equiv) were suspended in 1.5 mL DMF. Et3N (0.106 mL, 0.761 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 triturated with EtOAc and CH2Cl2, filtered, and washed with CH2Cl2 to provide 69 mg (26%) of the title compound as an off white solid. MS (ES+) m/e 413 [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 triturated with EtOAc and CH2Cl2
  7. filtrationfiltered
  8. washwashed with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-6bf4fd21fc2440b6bc7b48a9f91bcecc
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07592357B2

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