Benzyl 3-aminobenzoate → 3-{[5-(2-Adamantan-1-yl-ethyl)-2-naphthalen-2-yl-1H-imidazole-4-carbonyl]-amino}-benzoic Acid

HRID 1018314

Reaktionsgleichung

Reaktionsgleichung von HRID 1018314
[C:1]12([CH2:11][CH2:12][C:13]3[NH:17][C:16]([C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[CH:19]=4)=[N:15][C:14]=3[C:28](O)=[O:29])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([O:38][C:39](=[O:47])[C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([NH2:46])[CH:41]=1)C1C=CC=CC=1>>[C:1]12([CH2:11][CH2:12][C:13]3[NH:17][C:16]([C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[CH:19]=4)=[N:15][C:14]=3[C:28]([NH:46][C:42]3[CH:41]=[C:40]([CH:45]=[CH:44][CH:43]=3)[C:39]([OH:47])=[O:38])=[O:29])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Komponenten

3

Edukt 2

HCID 15428374Benzyl 3-aminobenzoateHCID 184054925-(2-Adamantan-1-yl-ethyl)-2-naphthalen-2-yl-1H-imidazole-4-carboxylic acid

Produkt 1

HCID 184054433-{[5-(2-Adamantan-1-yl-ethyl)-2-naphthalen-2-yl-1H-imidazole-4-carbonyl]-amino}-benzoic Acid

Versuchsvorschrift

5-(2-Adamantan-1-yl-ethyl)-2-naphthalen-2-yl-1H-imidazole-4-carboxylic acid (Example 44) was reacted with 3-amino-benzoic acid benzyl ester according to the procedure of Example 20, step d. The benzyl ester was deprotected according to the procedure of Example 20, step e to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 12.91 (1H, br s), 9.90 (1H, br s), 8.54 (2H, d), 8.27 (1H, dd), 8.04-7.94 (4H, m), 7.65-7.44 (4H, m), 3.04 (2H, m), 1.98 (3H, br s), 1.66 (6H, m), 1.58 (6H, s), 1.45 (2H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 63.85; H, 7.57; N, 7.80%; C40H50N4O8.1.9 H2O requires: C, 64.12; H, 7.24; N, 7.48%.

Quellen und Nachweise

ORD-Eintrag
ord-7d8bdcbebcaf4588954c421f1ac3afdb
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479531B1

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