4-Pyridinecarboxaldehyde → HCID 54402970, compound

HRID 1018339Notes

Reaction equation

HRID 1018339 reaction equation
[C:1]12([CH2:11][CH2:12][C:13]3[NH:17][C:16]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)=[N:15][C:14]=3[C:24]([OH:26])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.N1C=CC(C=O)=CC=1.[CH2:35]([O:42][C:43](=[O:51])[C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([NH2:50])[CH:45]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[CH2:35]([O:42][C:43](=[O:51])[C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([NH:50][C:24]([C:14]2[N:15]=[C:16]([C:18]3[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=3)[NH:17][C:13]=2[CH2:12][CH2:11][C:1]23[CH2:8][CH:7]4[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]4)[CH2:2]2)[CH2:10]3)=[O:26])[CH:45]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

4

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 15428374Benzyl 3-aminobenzoateHCID 18405639HCID 18405639, compound

Product 1

HCID 54402970HCID 54402970, compound

Procedure

5-(2-Adamantan-1-yl-ethyl)-2-pyridine-4-yl-1H-imidazole-4-carboxylic acid (prepared according to the procedure of Example 70, steps a and b, with the modification that pyridine-4-carboxaldehyde was used instead of 2-dimethylamino-benzaldehyde in step a) was reacted with 3-amino-benzoic acid benzyl ester according to the procedure of Example 177, step a to afford 3-{[5-(2-adamantan-1-yl-ethyl)-2-pyridine-4-yl-1H-imidazole-4-carbonyl]-amino}-benzoic acid benzyl ester. The benzyl group was removed following the procedure of Example 1, step e, to afford the title compound as a white solid. 1H NMR (300 MHz, d6-DMSO) 13.20 (1H, br s), 9.88 (1H, s), 8.67 (2H, dd), 8.47 (1H, s), 8.00 (3H, m), 7.64 (1H, d), 7.41 (1H, t), 3.01 (2H, m), 1.95 (3H, br s), 1.65 (6H, m), 1.55 (6H, s), 1.44 (2H, m). The product was converted to the maleic acid salt and lyophilised from water/dioxan. Found: C, 60.81; H, 6.48; N, 8.95%. C32H34N4O7.2.5 mols H2O requires: C, 60.85; H, 6.22; N, 8.87%.

Sources & evidence

ORD record
ord-6718f3809d2e4035b579520779ab076e
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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