Triethylamine → N-cyclopropyl-4'-[5-(cyclopropylmethyl)-1,3,4-oxadiazol-2-yl]-6-methyl-1,1'-biphenyl-3-carboxamide

HRID 31493

Reaktionsgleichung

Reaktionsgleichung von HRID 31493
N([CH2:4][C:5]1[O:9][C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[C:21]([CH3:22])=[CH:20][CH:19]=[C:18]([C:23]([NH:25][CH:26]4[CH2:28][CH2:27]4)=[O:24])[CH:17]=3)=[CH:12][CH:11]=2)=[N:7][N:6]=1)=[N+]=[N-].C(N(CC)CC)C.Cl.[CH:37]1(CC(=N)OCC)[CH2:39][CH2:38]1>C(O)C>[CH:26]1([NH:25][C:23]([C:18]2[CH:17]=[C:16]([C:13]3[CH:12]=[CH:11][C:10]([C:8]4[O:9][C:5]([CH2:4][CH:37]5[CH2:39][CH2:38]5)=[N:6][N:7]=4)=[CH:15][CH:14]=3)[C:21]([CH3:22])=[CH:20][CH:19]=2)=[O:24])[CH2:28][CH2:27]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 14860732HCID 14860732, VerbindungHCID 866046954'-[5-(azidomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide2×

Produkt 1

HCID 10474498N-cyclopropyl-4'-[5-(cyclopropylmethyl)-1,3,4-oxadiazol-2-yl]-6-methyl-1,1'-biphenyl-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4′-[5-(Azidomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 44) (40 mg), triethylamine (0.051 ml) and ethyl 2-cyclopropylethanimidate hydrochloride (23 mg) in ethanol (3 ml) were heated at 80° C. for 16 hours. The ethanol was removed under vacuum, the residue applied to a bond-elut (silica) and eluted with an ethyl acetate/cyclohexane gradient. Evaporation of the solvent from the product fractions gave N-cyclopropyl-4′-[5-(cyclopropylmethyl)-1,3,4-oxadiazol-2-yl]-6-methyl-1,1′-biphenyl-3-carboxamide.

Aufarbeitung

  1. customThe ethanol was removed under vacuum
  2. washeluted with an ethyl acetate/cyclohexane gradient
  3. customEvaporation of the solvent from the product fractions

Quellen und Nachweise

ORD-Eintrag
ord-efdd542b76c8492f8dc34770b14b5bac
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425555B2

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