5-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carboxylic acid → 3-{[5-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carbonyl]-amino}-2,6-dimethyl-benzoic Acid Methyl Ester
Reaktionsgleichung
[C:1]12([CH2:11][CH2:12][C:13]3[NH:17][C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[CH3:24])=[N:15][C:14]=3[C:25](O)=[O:26])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:28][O:29][C:30](=[O:40])[C:31]1[C:36]([CH3:37])=[CH:35][CH:34]=[C:33]([NH2:38])[C:32]=1[CH3:39]>>[CH3:28][O:29][C:30](=[O:40])[C:31]1[C:36]([CH3:37])=[CH:35][CH:34]=[C:33]([NH:38][C:25]([C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])[NH:17][C:13]=2[CH2:12][CH2:11][C:1]23[CH2:10][CH:5]4[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]4)[CH2:8]2)[CH2:2]3)=[O:26])[C:32]=1[CH3:39]Komponenten
3
Versuchsvorschrift
5-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole4-carboxylic acid (Example 93) (374 mg, 1.00 mmol) was reacted with 3-amino-2,6-dimethyl-benzoic acid methyl ester (prepared from 2,6-dimethyl-benzoic acid by nitration, esterification and reduction) (179 mg, 1.00 mmol) according to the procedure of Example 20, step d. The crude product was purified by flash chromatography (silica, hexane/ethyl acetate 2:1) to afford colourless foam (344 mg, 64%). 1H NMR (300 MHz, CDCl3) 9.32 (1H, br s), 9.22 (1H, br s), 8.12 (1H, d), 7.55 (1H, d), 7.29 (3H, m), 7.08 (1H, d), 3.92 (3H, s), 3.12 (2H, m) 2.63 (3H, s), 2.28 (6H, s), 1.97 (3H, s), 1.74-1.44 (14H, m).
Aufarbeitung
- customThe crude product was purified by flash chromatography (silica, hexane/ethyl acetate 2:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-24f71364c437473cb8228c3ecbc67e46
- Quelldatensatz
- uspto-grants-2002_11
- Patentnummer
- US06479531B1
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