HCID 18405518, compound → HCID 18405427, compound

HRID 1018361Notes

Reaction equation

HRID 1018361 reaction equation
[C:1]12([CH2:11][CH2:12][C:13]3[NH:17][C:16]([CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[N:15][C:14]=3[C:24](O)=[O:25])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C[O:28][C:29](=[O:39])[CH:30]=[CH:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([NH2:38])[CH:33]=1>>[C:1]12([CH2:11][CH2:12][C:13]3[NH:17][C:16]([CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]4)=[N:15][C:14]=3[C:24]([NH:38][C:34]3[CH:33]=[C:32](/[CH:31]=[CH:30]/[C:29]([OH:28])=[O:39])[CH:37]=[CH:36][CH:35]=3)=[O:25])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

3

Reactant 2

HCID 18405518HCID 18405518, compoundHCID 54385173Methyl 3-aminocinnamate

Product 1

HCID 18405427HCID 18405427, compound

Procedure

5-(2-Adamantan-1-yl-ethyl)-2-cyclohexyl-1H-imidazole-4-carboxylic acid (Example 252) was reacted with 3-(3-amino-phenyl)-acrylic acid methyl ester (prepared in two steps from 3-nitro-benzaldehyde) according to the procedure of Example 20, step d. The methyl ester was hydrolysed using the same procedure as in Example 36, step d to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 12.00 (1H, br s), 9.55 (1H, br s), 8.00 (1H, s), 7.86 (1H, m), 7.57 (1H, d), 7.36 (2H, m), 6.50 (1H, d), 2.89 (2H, m), 2.68 (1H, m), 1.94 (5H, br s), 1.80-1.51 (17H, m), 1.39-1.19 (5H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 60.52; H, 8.50; N, 7.59%. C38H56N4O8.3.0 mols H2O requires: C, 60.78; H, 8.32; N, 7.46%.

Sources & evidence

ORD record
ord-4254c27569894fd2ab90c21267e51c90
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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