HCID 18405518, compound → HCID 18405559, compound

HRID 1018359Notes

Reaction equation

HRID 1018359 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]([OH:26])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([O:29][C:30](=[O:41])[C:31]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([NH2:40])[CH:35]=1)([CH3:33])[CH3:32])C>>[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:40][C:36]3[CH:35]=[C:34]([C:31]([CH3:33])([CH3:32])[C:30]([OH:41])=[O:29])[CH:39]=[CH:38][CH:37]=3)=[O:26])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

3

Reactant 2

HCID 18405518HCID 18405518, compoundHCID 54070153HCID 54070153, compound

Product 1

HCID 18405559HCID 18405559, compound

Procedure

5-(2-Adamantan-1-yl-ethyl)-2-cyclohexyl-1H-imidazole-4-carboxylic acid (Example 252) was reacted with 2-(3-amino-phenyl)-2-methyl-propionic acid ethyl ester (prepared from 2-(4-chloro-phenyl)-2-methyl-propionic acid using Mutti's procedure (S. Mutti et al. Synth. Comm. 1997, 27, 425)) according to the procedure of Example 20, step d. The ethyl ester was hydrolysed using the same procedure as in Example 247, step b to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 10.52 (1H, br s), 7.70 (2H, m), 7.32 (1H, m), 7.12 (1H, d), 2.93 (3H, m), 1.98-1.35 (33H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 63.89; H, 8.61; N, 7.77%; C39H60N4O8.1.0 mol H2O requires: C, 64.09; H, 8.55; N, 7.67%.

Sources & evidence

ORD record
ord-29f7f4b3c2254e9a8047249e150f0da4
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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