Cyclohexanecarboxaldehyde → HCID 57257056, compound

HRID 1018351Notes

Reaction equation

C1(C=O)CCC=CCC1.[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[CH2:41][CH2:40][CH:39]=[CH:38][CH2:37][CH2:36]4)=[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.[CH3:45][O:46][C:47](=[O:55])[C:48]1[CH:53]=[CH:52][CH:51]=[C:50]([NH2:54])[CH:49]=1>>[CH2:16]([O:17][C:42]([C:31]1[N:32]=[C:33]([CH:35]2[CH2:41][CH2:40][CH:39]=[CH:38][CH2:37][CH2:36]2)[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.[CH3:45][O:46][C:47](=[O:55])[C:48]1[CH:53]=[CH:52][CH:51]=[C:50]([NH:54][C:42]([C:31]2[N:32]=[C:33]([CH:35]3[CH2:41][CH2:40][CH:39]=[CH:38][CH2:37][CH2:36]3)[NH:34][C:30]=2[CH2:29][O:28][C:18]23[CH2:27][CH:22]4[CH2:21][CH:20]([CH2:26][CH:24]([CH2:23]4)[CH2:25]2)[CH2:19]3)=[O:44])[CH:49]=1

Participants

Reactant 4

HCID 16275Cyclohexanecarboxaldehyde

HCID 78274Benzoic acid, 3-amino-, methyl ester

HCID 13546170HCID 13546170, compound

HCID 18405331HCID 18405331, compound

Product 2

HCID 57257056HCID 57257056, compound

HCID 69686438HCID 69686438, compound

Procedure

5-(Adamantan-1-yloxymethyl)-2-cyclohept-4-enyl-1H-imidazole-4-carboxylic acid benzyl ester was prepared according to the procedure of Example 216, steps a, b, c, d with the modification that cyclohept-4-enecarboxaldehyde (D. F. Murray et al. J. Org Chem. 1986, 51, 1) 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-cyclohept-4-enyl-1H-imidazole-4-carboxylic acid was reacted with 3-amino-benzoic acid methyl ester according to the procedure of Example 20, step d to afford 3-{[5-(adamantan-1-yloxymethyl)-2-cyclohept-4-enyl-1H-imidazole-4-carbonyl]-amino}-benzoic acid methyl ester. The methyl ester was hydrolysed according to the procedure of Example 36, step d to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 12.90 (1H, br s), 12.40 (1H, br s), 9.87 (1H, br s), 8.44 (1H, s), 7.93 (1H, d), 7.63 (1H, d), 7.42 (1H, t), 5.81 (2H, m), 4.79 (2H, s), 3.04 (1H, m), 2.30 (2H, m), 2.11 (5H, m), 1.96 (2H, m), 1.76-1.53 (14H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 59.69; H, 7.90; N, 7.88%. C36H52N4O9.2.1 mols H2O requires: C, 59.81; H, 7.84; N, 7.75%.

Sources & evidence

ORD record: ord-c6dd568236804748a93b89062d7a5d10
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479531B1

Reaction notes

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