Benzaldehyde → 3-[(5-Cycloheptylmethyl-2-phenyl-1H-imidazole-4-carbonyl)-amino]-benzoic Acid

HRID 1018311

Reaction equation

HRID 1018311 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:9]1C2C(=CC=CC=2)C=C[C:10]=1C=O.C(O[C:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([NH2:36])[CH:31]=1)C1C=CC=CC=1.C(OC(=O)[C:47]1[CH:62]=[C:61]([NH2:63])[CH:60]=[C:49]([C:50]([O:52]CC2C=CC=CC=2)=[O:51])[CH:48]=1)C1C=CC=CC=1.C[NH:66][CH2:67][C@@H:68]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[OH2:78]>O.O1CCOCC1>[CH:30]1([CH2:31][C:32]2[NH:36][C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:66][C:67]=2[C:68]([NH:63][C:61]2[CH:60]=[C:49]([CH:48]=[CH:47][CH:62]=2)[C:50]([OH:52])=[O:51])=[O:78])[CH2:29][CH2:10][CH2:9][CH2:33][CH2:34][CH2:35]1

Participants

8

Reactant 6

HCID 240BenzaldehydeHCID 962WaterHCID 62012-NaphthalenecarboxaldehydeHCID 8567N-Methyl-D-glucamineHCID 7023592Dibenzyl 5-aminoisophthalateHCID 15428374Benzyl 3-aminobenzoate

Product 1

HCID 184055563-[(5-Cycloheptylmethyl-2-phenyl-1H-imidazole-4-carbonyl)-amino]-benzoic Acid

Reagents, catalysts & solvents 1

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

Procedure

The title compound was prepared according to the procedure of Example 20, with the modification that benzaldehyde was used in step b instead of 2-naphthaldehyde and 3-amino-benzoic acid benzyl ester was used in step d instead of 5-amino-isophthalic acid dibenzyl ester. 1H NMR (300 MHz, d6-DMSO) 13.00 (1H, br s), 9.86 (1H, s), 8.51 (1H, s), 8.07 (2H, d), 7.99 (1H, d), 7.63 (1H, d), 7.42 (4H, m), 2.94 (2H, d), 1.98 (1H, m), 1.66-1.22 (12H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 59.97; H, 7.32; N, 8.72%; C32H44N4O8.1.5 H2O requires: C, 60.04; H, 7.41; N, 8.75%.

Sources & evidence

ORD record
ord-99c84be22dff4bb2b234d079077bc450
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Linked notes

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