Sodium hydride → 3-tert-butyl-4-chloro-N-(6-(2-chlorophenyl)-2-methoxy-3-nitropyridin-4-yl)-1-methyl-1H-pyrazole-5-carboxamide

HRID 570268

Reaktionsgleichung

Reaktionsgleichung von HRID 570268
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([O:14][CH3:15])[C:11]([N+:16]([O-:18])=[O:17])=[C:10]([NH2:19])[CH:9]=1.[H-].[Na+].[C:22]([C:26]1[C:27]([Cl:35])=[C:28]([C:32](O)=[O:33])[N:29]([CH3:31])[N:30]=1)([CH3:25])([CH3:24])[CH3:23].C(Cl)(=O)C(Cl)=O>C1COCC1.C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([O:14][CH3:15])[C:11]([N+:16]([O-:18])=[O:17])=[C:10]([NH:19][C:32]([C:28]2[N:29]([CH3:31])[N:30]=[C:26]([C:22]([CH3:24])([CH3:23])[CH3:25])[C:27]=2[Cl:35])=[O:33])[CH:9]=1

Komponenten

8

Edukt 4

HCID 24758Sodium hydrideHCID 65578Oxalyl chlorideHCID 584254493-tert-butyl-4-chloro-1-methyl-1H-pyrazole-5-carboxylic acidHCID 674116886-(2-Chlorophenyl)-2-methoxy-3-nitropyridin-4-amine

Produkt 1

HCID 674096383-tert-butyl-4-chloro-N-(6-(2-chlorophenyl)-2-methoxy-3-nitropyridin-4-yl)-1-methyl-1H-pyrazole-5-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 6-(2-chloro-phenyl)-2-methoxy-3-nitro-pyridin-4-ylamine (8.10 g, 29.0 mmol, prepared as described in the previous step) in THF (200 mL) was treated with NaH (3.47 g, 86.8 mmol, 60% dispersion in oil) at 0° C. for 1 h. Simultaneously a solution of 5-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid (6.90 g, 31.8 mmol, prepared as described in Example B) in DCM (200 mL) was treated with oxalyl chloride (3.2 mL, 36 mmol) and DMF (50 μL) at 0° C. and stirred at room temperature for 1 h. The volatile components were removed in vacuo, and the resulting residue was dried in vacuo for 15 min taken up in THF (20 mL) and added to the above sodium anilide solution at 0° C. The resulting mixture was stirred at room temperature for 30 min, quenched with saturated aqueous NH4Cl (20 mL), and extracted with EtOAc (3×100 mL). The combined extracts were dried over MgSO4 and concentrated in vacuo. The resulting solid was suspended in hexane (200 mL) and sonicated for 10 min and collected by suction filtration to yield 5-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [6-(2-chloro-phenyl)-2-methoxy-3-nitro-pyridin-4-yl]-amide as a tan-colored solid.

Aufarbeitung

  1. customThe volatile components were removed in vacuo
  2. customthe resulting residue was dried in vacuo for 15 min
  3. additionadded to the above sodium anilide solution at 0° C
  4. stirringThe resulting mixture was stirred at room temperature for 30 min
  5. customquenched with saturated aqueous NH4Cl (20 mL)
  6. extractionextracted with EtOAc (3×100 mL)
  7. dry with materialThe combined extracts were dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customsonicated for 10 min
  10. filtrationcollected by suction filtration

Quellen und Nachweise

ORD-Eintrag
ord-c4190c57ad124421a463776f2107a50d
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023846B2

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