Water → 5-{[5-(2-Cycloheptyl-ethyl)-2-cyclohexyl-1h-imidazole-4-carbonyl]-amino}-2-methyl-benzoic acid

HRID 1018336Notes

Reaction equation

HRID 1018336 reaction equation
[CH:1]1([CH2:8][CH2:9][C:10](O)=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:13]1([CH:19]=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)C=CC=1C=O.C([O:40][C:41](=[O:50])[C:42]1[CH:47]=[C:46]([NH2:48])[CH:45]=[CH:44][C:43]=1[CH3:49])C1C=CC=CC=1.C(OC(=O)C1C=C([NH2:76])C=C(C(OCC2C=CC=CC=2)=O)C=1)C1C=CC=CC=1.C[NH:79][CH2:80][C@@H:81]([C@H]([C@@H]([C@@H](CO)O)O)O)[OH:82].[OH2:91]>O.O1CCOCC1>[CH:1]1([CH2:8][CH2:9][C:10]2[NH:48][C:19]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]3)=[N:79][C:80]=2[C:81]([OH:82])=[O:91])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1.[CH:1]1([CH2:8][CH2:9][C:10]2[NH:76][C:21]([CH:30]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)=[N:79][C:80]=2[C:81]([NH:48][C:46]2[CH:45]=[CH:44][C:43]([CH3:49])=[C:42]([CH:47]=2)[C:41]([OH:40])=[O:50])=[O:82])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

10

Reactant 7

HCID 962WaterHCID 62012-NaphthalenecarboxaldehydeHCID 8567N-Methyl-D-glucamineHCID 16275CyclohexanecarboxaldehydeHCID 7023592Dibenzyl 5-aminoisophthalateHCID 151069953-Cycloheptylpropanoic acidHCID 538373385-Amino-2-methyl-benzoic acid benzyl ester

Product 2

HCID 184053485-{[5-(2-Cycloheptyl-ethyl)-2-cyclohexyl-1h-imidazole-4-carbonyl]-amino}-2-methyl-benzoic acidHCID 184056825-(2-Cycloheptyl-ethyl)-2-cyclohexyl-1h-imidazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

5-(2-Cycloheptyl-ethyl)-2-cyclohexyl-1H-imidazole-4-carboxylic acid was prepared according to the procedure of Example 20, steps a, b and c, with the modification that cycloheptanepropionic acid was used instead of cycloheptaneacetic acid in step a, and cyclohexanecarboxaldehyde replaced 2-naphthaldehyde in step b. The acid was then converted to the title compound according to the procedure of Example 20, steps d and e, with the modification that 5-amino-2-methyl-benzoic acid benzyl ester replaced 5-amino-isophthalic acid dibenzyl ester in step d. 1H NMR (300 MHz, d6-DMSO) 11.90 (1H, br s), 9.46 (1H, s), 8.29 (1H, d), 7.74 (1H, dd), 7.19 (1H, d), 2.92 (2H, m), 2.70 (1H, m), 2.45 (3H, s), 1.90 (2H, m), 1.75-1.35 (23H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 60.04; H, 8.78; N, 8.44%. C34H54N4O8.1.8 mols H2O requires: C, 60.05; H, 8.55; N, 8.24%.

Sources & evidence

ORD record
ord-6a7c7df5818b48efaa897f93257c5b98
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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