Tetrahydrofuran → 2-[3-(2,2-Difluoro-benzo[1,3]dioxol-5-ylamino)-5-(2,6-dimethyl-pyridin-4-yl)-[1,2,4]-triazol-1-yl]-N-ethyl-acetamide

HRID 1952184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1952184
Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:12]([CH2:13][C:14]([NH:16][CH2:17][CH3:18])=[O:15])[N:11]=[C:10]([NH:19][C:20]3[CH:30]=[CH:29][C:23]4[O:24][C:25]([F:28])([F:27])[O:26][C:22]=4[CH:21]=3)[N:9]=2)[CH:5]=[C:4]([CH3:31])[N:3]=1.[CH2:32]1COCC1.CN1CCCC1=O.C[Mg+].[Br-]>C(OCC)C.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3].CO>[F:27][C:25]1([F:28])[O:24][C:23]2[CH:29]=[CH:30][C:20]([NH:19][C:10]3[N:9]=[C:8]([C:6]4[CH:5]=[C:4]([CH3:31])[N:3]=[C:2]([CH3:32])[CH:7]=4)[N:12]([CH2:13][C:14]([NH:16][CH2:17][CH3:18])=[O:15])[N:11]=3)=[CH:21][C:22]=2[O:26]1

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 13387N-methyl-2-pyrrolidoneHCID 594977652-[5-(2-Chloro-6-methyl-pyridin-4-yl)-3-(2,2-difluoro-benzo[1,3]dioxol-5-ylamino)-[1,2,4]triazol-1-yl]-N-ethyl-acetamideHCID 178418689HCID 178418689, Verbindung

Produkt 1

HCID 252296152-[3-(2,2-Difluoro-benzo[1,3]dioxol-5-ylamino)-5-(2,6-dimethyl-pyridin-4-yl)-[1,2,4]-triazol-1-yl]-N-ethyl-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 5483663Ferric acetylacetonateKatalysatorHCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Intermediate D4 (0.70 g; 0.0016 mol), Iron(III) acetylacetonate (0.067 g; 0.0002 mol), THF (20 ml) and 1-methyl-2-pyrrolidinone (5 ml) were stirred at 0° C. under N2. Excess CH3MgBr in diethyl ether (2 M) was added and the mixture was brought to room temperature. The reaction mixture was then decomposed with CH3OH and evaporated in vacuo. Water and CH2Cl2 were added and the mixture was filtered over dicalite. The filtrate was evaporated and water and DIPE were added. The precipitate was filtered off, dissolved in CH2Cl2, dried over MgSO4, filtered and evaporated in vacuo. The residue was stirred in water, the precipitate was filtered off and dried. Yield: 400 mg of compound E1. melting point: 242.28° C. LCMS Retention time: 5.12; [M+H]+peak: 431; LCMS procedure 1

Aufarbeitung

  1. customwas brought to room temperature
  2. customevaporated in vacuo
  3. additionWater and CH2Cl2 were added
  4. filtrationthe mixture was filtered over dicalite
  5. customThe filtrate was evaporated
  6. additionwater and DIPE were added
  7. filtrationThe precipitate was filtered off
  8. dissolutiondissolved in CH2Cl2
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. filtrationthe precipitate was filtered off
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-85917e8bc3134eb0851f7a20ed506ba2
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404851B2

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