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

HRID 1018353ノート

反応式

HRID 1018353 の反応式
[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]

参加物

3

反応物 2

HCID 184053605-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carboxylic acidHCID 19781624Methyl 3-amino-2,6-dimethylbenzoate

生成物 1

HCID 701608823-{[5-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carbonyl]-amino}-2,6-dimethyl-benzoic Acid Methyl Ester収率 65.4%

実験手順

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).

後処理

  1. customThe crude product was purified by flash chromatography (silica, hexane/ethyl acetate 2:1)

出典と根拠

ORDレコード
ord-24f71364c437473cb8228c3ecbc67e46
出典データセット
uspto-grants-2002_11
特許番号
US06479531B1

反応ノート

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