Cyclohexanecarboxaldehyde → HCID 69686100, compound

HRID 1018350Notes

Reaction equation

[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(O[C:15]([C:17]12[CH2:24][CH2:23][CH:20]([CH2:21][CH2:22]1)[CH:19]=[CH:18]2)=O)C.[CH:25]1([CH:31]=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.[C:33]12([O:43][CH2:44][C:45]3[NH:49][C:48]([C:50]45[CH2:57][CH2:56][CH:53]([CH2:54][CH2:55]4)[CH:52]=[CH:51]5)=[N:47][C:46]=3[C:58]([OH:60])=[O:59])[CH2:42][CH:37]3[CH2:38][CH:39]([CH2:41][CH:35]([CH2:36]3)[CH2:34]1)[CH2:40]2.[CH2:61]([O:68][C:69](=[O:77])[C:70]1[CH:75]=[CH:74][CH:73]=[C:72]([NH2:76])[CH:71]=1)[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1>>[CH2:31]([O:32][C:58]([C:46]1[N:47]=[C:48]([C:50]23[CH2:57][CH2:56][CH:53]([CH2:54][CH2:55]2)[CH:52]=[CH:51]3)[NH:49][C:45]=1[CH2:44][O:43][C:33]12[CH2:42][CH:37]3[CH2:38][CH:39]([CH2:41][CH:35]([CH2:36]3)[CH2:34]1)[CH2:40]2)=[O:59])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH2:61]([O:68][C:69](=[O:77])[C:70]1[CH:75]=[CH:74][CH:73]=[C:72]([NH:76][C:58]([C:46]2[N:47]=[C:15]([C:17]34[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24]3)[CH:19]=[CH:18]4)[NH:49][C:45]=2[CH2:44][O:43][C:33]23[CH2:42][CH:37]4[CH2:38][CH:39]([CH2:41][CH:35]([CH2:36]4)[CH2:34]2)[CH2:40]3)=[O:60])[CH:71]=1)[C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1

Participants

Reactant 5

HCID 16275Cyclohexanecarboxaldehyde

HCID 13735241Ethyl bicyclo[2.2.2]oct-2-ene-1-carboxylate

HCID 15428374Benzyl 3-aminobenzoate

HCID 18405441HCID 18405441, compound

HCID 178418287HCID 178418287, compound

Product 2

HCID 69686100HCID 69686100, compound

HCID 69686231HCID 69686231, compound

Procedure

5-(Adamantan-1-yloxymethyl)-2-bicyclo[2.2.2]oct-2-en-1-yl-1H-imidazole-4-carboxylic acid benzyl ester was prepared according to the procedure of Example 216, steps a, b, c and d with the modification that bicyclo[2.2.2]oct-2-en-1-yl-carbaldehyde (prepared by reduction and then pyridinium chlorochromate oxidation of bicyclo[2.2.2]oct-2-en-1-yl-carboxylic acid ethyl ester (C. A. Grob, M. Ohta, E. Renk and A. Weiss, Helv. Chim. Acta 1958, 41, 1191)) 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[2.2.2]oct-2-en-1-yl-1H-imidazole4-carboxylic acid was reacted with 3-amino-benzoic acid benzyl ester according to the procedure of Example 177, step a to afford 3-{[5-(adamantan-1-yloxymethyl)-2-bicyclo[2.2.2]oct-2-en-1-yl-1H-imidazole4-carbonyl]-amino}-benzoic acid benzyl ester. The benzyl ester was hydrolysed according to the procedure of Example 211, step b to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 12.35 (1H, br s), 9.69 (1H, s), 8.44 (1H, br s), 7.95 (1H, d), 7.62 (1H, d), 7.41 (1H, t), 6.73 (1H, d), 6.38 (1H, dd), 4.81 (2H, s), 2.63 (1H, br s), 2.11 (3H, br s), 1.97 (2H, td), 1.76 (6H, s), 1.67-1.53 (8H, m), 1.44 (2H, t), 1.30 (2H, t). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 56.61; H, 7.99; N, 7.35%. C37H52N4O9.5.0 mols H2O requires: C, 56.47; H, 7.94; N, 7.12%.

Workup

customprepared by reduction

Sources & evidence

ORD record: ord-3cf50e091931477bbfb344a099c0cb9e
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479531B1

Reaction notes

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