Cyclohexanecarboxaldehyde → HCID 57012568, compound

HRID 1018382Notes

Reaction equation

C12C(C=O)C(CC1)=CC=2.[CH:10]1([CH:16]=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[C:18]12([O:28][CH2:29][C:30]3[NH:34][C:33]([CH:35]4[CH:39]5[CH:40]=[CH:41][CH:36]4[CH:37]=[CH:38]5)=[N:32][C:31]=3[C:42]([OH:44])=[O:43])[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2.[CH2:45]([O:52][C:53](=[O:61])[C:54]1[CH:59]=[CH:58][CH:57]=[C:56]([NH2:60])[CH:55]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>>[CH2:16]([O:17][C:42]([C:31]1[N:32]=[C:33]([CH:35]2[CH:36]3[CH:37]=[CH:38][CH:39]2[CH:40]=[CH:41]3)[NH:34][C:30]=1[CH2:29][O:28][C:18]12[CH2:25][CH:24]3[CH2:26][CH:20]([CH2:21][CH:22]([CH2:23]3)[CH2:27]1)[CH2:19]2)=[O:43])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:45]([O:52][C:53](=[O:61])[C:54]1[CH:59]=[CH:58][CH:57]=[C:56]([NH:60][C:42]([C:31]2[N:32]=[C:33]([CH:35]3[CH:39]4[CH:40]=[CH:41][CH:36]3[CH:37]=[CH:38]4)[NH:34][C:30]=2[CH2:29][O:28][C:18]23[CH2:27][CH:22]4[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]4)[CH2:19]2)[CH2:25]3)=[O:44])[CH:55]=1)[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1

Participants

Reactant 4

HCID 16275Cyclohexanecarboxaldehyde

HCID 15428374Benzyl 3-aminobenzoate

HCID 18405349HCID 18405349, compound

HCID 18405473HCID 18405473, compound

Product 2

HCID 57012568HCID 57012568, compound

HCID 69686526HCID 69686526, compound

Procedure

5-(Adamantan-1-yloxymethyl)-2-bicyclo[2.2.1]hepta-2,5-dien-7-yl-1H-imidazole4-carboxylic acid benzyl ester was prepared according to the procedure of Example 216, steps a, b, c and d with the modification that norbornadiene-7-carboxaldehyde (J. Stapersma and G. W. Klumpp Tetrahedron, 1981, 37, 187) was used in step d instead of cyclohexanecarboxaldehyde. The benzyl ester was hydrolysed according to the procedure of Example 211, step b and the resulting 5-(adamantan-1-yloxymethyl)-2-bicyclo[2.2.1]hepta-2,5-dien-7-yl-1H-imidazole-4-carboxylic acid was reacted with 3-amino-benzoic acid benzyl ester according to the procedure of Example 20, step d to afford 3-{[5-(adamantan-1-yloxymethyl)-2-bicyclo[2.2.1]hepta-2,5-dien-7-yl-1H-imidazole-4-carbonyl]-amino}-benzoic acid benzyl ester. The benzyl ester was hydrolysed according to the procedure of Example 211, step b and the crude product was purified by flash column chromatography (silica, DCM/methanol 95:5 ) to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 12.10 (1H, br s), 9.65 (1H, br s), 8.42 (1H, br s), 7.92 (1H, d), 7.62 (1H, d), 7.41 (1H, t), 6.90 (2H, s), 6.59 (2H, s), 4.75 (2H, s), 4.06 (2H, s), 3.47 (1H, s), 2.10 (3H, br s), 1.75 (6H, s), 1.58 (6H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 58.71; H, 7.44; N, 7.50%. C36H48N4O9.3.0 mols H2O requires: C, 58.84; H, 7.41; N, 7.62%.

Sources & evidence

ORD record: ord-15e970efe61043548c37b9c20e8af102
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479531B1

Reaction notes

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