5-Cycloheptylmethyl-2-naphthalen-2-yl-1H-imidazole-4-carboxylic Acid → 5-Cycloheptylmethyl-2-naphthalen-2-yl-1H-imidazole-4-carboxylic Acid (3,5-bis-methoxycarbonyloxymethyl-phenyl)-amide
Reaction equation
[CH:1]1([CH2:8][C:9]2[NH:13][C:12]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=3)=[N:11][C:10]=2[C:24](O)=[O:25])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:27][O:28][C:29]([O:31][CH2:32][C:33]1[CH:34]=[C:35]([CH:37]=[C:38]([CH2:40][O:41][C:42]([O:44][CH3:45])=[O:43])[CH:39]=1)[NH2:36])=[O:30]>>[CH3:45][O:44][C:42]([O:41][CH2:40][C:38]1[CH:37]=[C:35]([NH:36][C:24]([C:10]2[N:11]=[C:12]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=3)[NH:13][C:9]=2[CH2:8][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]2)=[O:25])[CH:34]=[C:33]([CH2:32][O:31][C:29]([O:28][CH3:27])=[O:30])[CH:39]=1)=[O:43]Participants
3
Reactant 2
Product 1
Procedure
5-Cycloheptylmethyl-2-naphthalen-2-yl-1H-imidazole-4-carboxylic acid (Example 20, step c) (605 mg, 1.75 mmol) was reacted with 3,5-bis-methoxycarbonyloxymethyl-aniline (492 mg, 1.75 mmol) according to the procedure of Example 20, step d to afford the product as a white solid (438 mg, 42%). 1H NMR (300 MHz, CDCl3) 9.42 (1H, br s), 9.35 (1H, s), 8.27 (1H, s), 8.06-7.89 (4H, m), 7.79 (2H, s), 7.56 (2H, m), 7.14 (1H, s), 5.18 (4H, s), 3.83 (6H, s), 3.12 (2H, d), 2.00-1.29 (13H, m).
Sources & evidence
- ORD record
- ord-63c8716bdf53448084f6e6c22590cce4
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479531B1
Reaction notes
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