2,6-Dichlorobenzaldehyde → HCID 69686289, compound

HRID 1018391Notes

Reaction equation

ClC1C=CC=C(Cl)C=1C=O.[CH:11]1([CH:17]=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[C:19]12([O:29][CH2:30][C:31]3[NH:35][C:34]([C:36]4[C:41]([Cl:42])=[CH:40][CH:39]=[CH:38][C:37]=4[Cl:43])=[N:33][C:32]=3[C:44](O)=[O:45])[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[CH2:20]1)[CH2:26]2.[CH3:47][O:48][C:49](=[O:57])[C:50]1[CH:55]=[CH:54][CH:53]=[C:52]([NH2:56])[CH:51]=1>>[CH2:17]([O:18][C:44]([C:32]1[N:33]=[C:34]([C:36]2[C:37]([Cl:43])=[CH:38][CH:39]=[CH:40][C:41]=2[Cl:42])[NH:35][C:31]=1[CH2:30][O:29][C:19]12[CH2:20][CH:21]3[CH2:22][CH:23]([CH2:24][CH:25]([CH2:27]3)[CH2:26]1)[CH2:28]2)=[O:45])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:47][O:48][C:49](=[O:57])[C:50]1[CH:55]=[CH:54][CH:53]=[C:52]([NH:56][C:44]([C:32]2[N:33]=[C:34]([C:36]3[C:37]([Cl:43])=[CH:38][CH:39]=[CH:40][C:41]=3[Cl:42])[NH:35][C:31]=2[CH2:30][O:29][C:19]23[CH2:20][CH:21]4[CH2:22][CH:23]([CH2:24][CH:25]([CH2:27]4)[CH2:26]2)[CH2:28]3)=[O:45])[CH:51]=1

Participants

Reactant 4

HCID 67372,6-Dichlorobenzaldehyde

HCID 16275Cyclohexanecarboxaldehyde

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

HCID 18405365HCID 18405365, compound

Product 2

HCID 69686289HCID 69686289, compound

HCID 69687721HCID 69687721, compound

Procedure

5-(Adamantan-1-yloxymethyl)-2-(2,6-dichloro-phenyl)-1H-imidazole-4-carboxylic acid benzyl ester was prepared according to the procedure of Example 216, steps a, b, c and d with the modification that 2,6-dichloro-benzaldehyde 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-(2,6-dichloro-phenyl)-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-(2,6-dichloro-phenyl)-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) 12.87 (2H, s), 10.00 (1H, s), 8.58 (1H, s), 7.94 (1H, d), 7.58 (4H, m), 7.39 (1H, t), 4.93 (2H, s), 2.11 (3H, s), 1.79 (6H, s), 1.58 (6H, s). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan.

Sources & evidence

ORD record: ord-634cf1fc0033461f8fa1489b1092a579
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479531B1

Reaction notes

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