4'-(2,6-Difluoro-benzoylamino)-6-methyl-biphenyl-3-carboxylic acid methyl ester → 2-(3-Iodo-4-methylphenyl)-1,3,4-oxadiazole

HRID 220757

Reaktionsgleichung

Reaktionsgleichung von HRID 220757
[I:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([NH:7][NH2:8])=[O:6].[CH3:13]OC(C1C=C(C2C=CC(NC(=O)C3C(F)=CC=CC=3F)=CC=2)C(C)=CC=1)=O>>[I:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][CH:13]=[N:8][N:7]=2)[CH:9]=[CH:10][C:11]=1[CH3:12]

Komponenten

3

Edukt 2

HCID 115526584'-(2,6-Difluoro-benzoylamino)-6-methyl-biphenyl-3-carboxylic acid methyl ester2×HCID 597325003-Iodo-4-methylbenzohydrazide2×

Produkt 1

HCID 586837712-(3-Iodo-4-methylphenyl)-1,3,4-oxadiazole

Versuchsvorschrift

3-Iodo-4-methyl benzoic acid methyl ester was treated with hydrazine to form 3-Iodo-4-methyl benzoic acid hydrazide. 2-(3-Iodo-4-methyl-phenyl)-[1,3,4]oxadiazole was prepared from 3-iodo-4-methyl benzoic acid hydrazide according to a method analogous to that described in J. of Medicinal Chemistry (2001), 44(8): 1268-85, the entire teachings of which are incorporated herein by reference. Compounds 46, 68, 69, 70, and 71 were prepared via an amide coupling reaction analogous to that described in step A of the synthesis of Compound 1, followed by a Suzuki coupling reaction analogous to that described in step B of the synthesis of Compound 1. The amide coupling reaction and Suzuki coupling reaction are shown for Compound 69 in Scheme XX below:

Aufarbeitung

  1. customfollowed by a Suzuki coupling reaction analogous to

Quellen und Nachweise

ORD-Eintrag
ord-b82e7bb0366e453f90934d3b33f3a803
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202999B2

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