HCID 18405518, compound → HCID 18405594, compound

HRID 1018356Notes

Reaction equation

HRID 1018356 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:34][C:35](=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([NH2:42])[C:37]=1[CH3:43])C1C=CC=CC=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:42][C:38]3[C:37]([CH3:43])=[C:36]([CH:41]=[CH:40][CH:39]=3)[C:35]([OH:44])=[O:34])=[O:26])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

3

Reactant 2

HCID 18405518HCID 18405518, compoundHCID 54141052Benzyl 3-amino-2-methylbenzoate

Product 1

HCID 18405594HCID 18405594, compound

Procedure

5-(2-Adamantan-1-yl-ethyl)-2-cyclohexyl-1H-imidazole-4-carboxylic acid (Example 252) was reacted with 3-amino-2-methyl-benzoic acid benzyl ester (prepared in two steps from 2-methyl-3-nitro-benzoic acid) according to the procedure of Example 20, step d. The benzyl ester was hydrogenated using the same procedure as in Example 1, step c to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 13.00 (1H, br s), 11.95 (1H, br s), 9.31 (1H, br s), 8.01 (1H, d), 7.49 (1H, d), 7.24 (1H, m), 2.85 (2H, m), 2.60 (1H, m), 2.39 (3H, s), 1.93-1.24 (27H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 62.84; H, 8.55; N, 7.80%. C37H56N4O8.1.0 mol H2O requires: C, 63.23; H, 8.32; N, 7.97%.

Sources & evidence

ORD record
ord-14ecc904e6ce4eb6a23f58c6d0c1e83a
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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