2-Chlorobenzimidazole → 4-[4'-(1H-Benzimidazol-2-ylamino)-1,1-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoic acid

HRID 9591

Reaktionsgleichung

Reaktionsgleichung von HRID 9591
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:23])[CH2:15][C:16]([CH3:22])([CH3:21])[C:17]([O:19]C)=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl[C:25]1[NH:29][C:28]2[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=2[N:26]=1.S1C2C=CC=CC=2N=C1NC1C=CC(C2C=CC(C(=O)CC(C)(C)C(O)=O)=CC=2)=CC=1>>[NH:26]1[C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[N:29]=[C:25]1[NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:23])[CH2:15][C:16]([CH3:21])([CH3:22])[C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Komponenten

4

Edukt 3

HCID 785722-ChlorobenzimidazoleHCID 114759304-[4'-(1,3-Benzothiazol-2-ylamino)-1,1'-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoic acidHCID 21985743Methyl 4-(4'-amino-1,1'-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate

Produkt 1

HCID 98018414-[4'-(1H-Benzimidazol-2-ylamino)-1,1-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoic acidAusbeute 48 %

Versuchsvorschrift

This compound was prepared from methyl 4-(4′-amino-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate (64 mg, 0.21 mmol) and 2-chloro-1H-benzimidazole (37.6 mg, 0.25 mmol) in a similar manner to the method described for 4-[4′-(1,3-benzothiazol-2-ylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoic acid, providing 40.7 mg (48%) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 12.00 (br s, 1 H), 11.05 (br s, 1 H), 8.05 (d, 2 H), 7.85 (m, 4 H), 7.65 (d, 2 H), 7.40 (m, 2 H), 7.10 (m, 2 H), 3.35 (s, 2 H), 1.25 (s, 6 H). LC-MS m/z 414.3 (MH+), ret. time 2.27 min.

Quellen und Nachweise

ORD-Eintrag
ord-c562ef6bea554331af07322689ed1205
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091228B2

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