Cyclohexanecarboxaldehyde → HCID 57257056, compound

HRID 1018352Notes

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.[CH2:45]([O:52][C:53](=[O:62])[CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[C:57]([NH2:61])[CH:56]=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[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.[CH2:45]([O:52][C:53](=[O:62])[CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[C:57]([NH:61][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[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]4)[CH2:19]2)[CH2:25]3)=[O:44])[CH:56]=1)[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1

Participants

Reactant 4

HCID 16275Cyclohexanecarboxaldehyde

HCID 13546170HCID 13546170, compound

HCID 18405331HCID 18405331, compound

HCID 19709480HCID 19709480, compound

Product 2

HCID 57257056HCID 57257056, compound

HCID 69686655HCID 69686655, 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-cyclohept4-enyl-1H-imidazole4-carboxylic acid was reacted with (3-amino-phenyl)-acetic acid benzyl 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}-phenyl)-acetic 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) 12.25 (2H, br m), 9.45 (1H, br s), 7.62 (2H, m), 7.24 (1H, t), 6.94 (1H, d), 5.82 (2H, br s), 4.78 (2H, s), 3.53 (2H, s), 3.03 (1H, m), 2.30 (2H, m), 2.13 (5H, m), 1.94 (2H, m), 1.76-1.58 (14H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 60.40; H, 8.07; N, 7.72%. C37H54N4O9.2.1 mols H2O requires: C, 60.38; H, 7.96; N, 7.61%.

Sources & evidence

ORD record: ord-a331034de8fc451cbcbd119631b70d89
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479531B1

Reaction notes

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