Potassium Iodide → N-Cyclopropyl-4'-{5-[(ethylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1'-biphenyl-3-carboxamide

HRID 31486

Reaktionsgleichung

Reaktionsgleichung von HRID 31486
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([C:21]([NH:23][CH:24]4[CH2:26][CH2:25]4)=[O:22])[CH:15]=3)=[CH:10][CH:9]=2)=[N:5][N:4]=1.[I-].[K+].[CH2:29]([NH2:31])[CH3:30]>C1COCC1>[CH:24]1([NH:23][C:21]([C:16]2[CH:15]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([C:6]4[O:7][C:3]([CH2:2][NH:31][CH2:29][CH3:30])=[N:4][N:5]=4)=[CH:9][CH:10]=3)[C:19]([CH3:20])=[CH:18][CH:17]=2)=[O:22])[CH2:26][CH2:25]1

Komponenten

5

Edukt 3

HCID 4875Potassium IodideHCID 6341EthylamineHCID 693148754'-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide2×

Produkt 1

HCID 11740259N-Cyclopropyl-4'-{5-[(ethylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1'-biphenyl-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4′-[5-(Chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 45) (37 mg) and potassium iodide (5 mg) were mixed in ethylamine in THF (2M, 3 ml) and the reaction stirred at room temperature for 18 hours. The excess amine was evaporated under vacuum and the residue purified by preparative HPLC. After evaporation of the solvent this gave N-cyclopropyl-4′-{5-[(ethylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1′-biphenyl-3-carboxamide.

Aufarbeitung

  1. customThe excess amine was evaporated under vacuum
  2. customthe residue purified by preparative HPLC
  3. customAfter evaporation of the solvent this gave N-cyclopropyl-4′-{5-[(ethylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1′-biphenyl-3-carboxamide

Quellen und Nachweise

ORD-Eintrag
ord-867f7ea46b1e48a3b08a2fde80b2da55
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425555B2

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