2-Chlorobenzaldehyde → HCID 57043039, compound

HRID 1018386Notes

Reaction equation

Cl[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C1(C=O)CCCCC1.[C:18]12([O:28][CH2:29][C:30]3[NH:34][C:33]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[Cl:41])=[N:32][C:31]=3[C:42](O)=[O:43])[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2.[CH3:45][O:46][C:47](=[O:55])[C:48]1[CH:53]=[CH:52][CH:51]=[C:50]([NH2:54])[CH:49]=1>>[CH2:4]([O:5][C:42]([C:31]1[N:32]=[C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[Cl:41])[NH:34][C:30]=1[CH2:29][O:28][C:18]12[CH2:19][CH:20]3[CH2:21][CH:22]([CH2:23][CH:24]([CH2:26]3)[CH2:25]1)[CH2:27]2)=[O:43])[C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:2]=1.[CH3:45][O:46][C:47](=[O:55])[C:48]1[CH:53]=[CH:52][CH:51]=[C:50]([NH:54][C:42]([C:31]2[N:32]=[C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[Cl:41])[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:43])[CH:49]=1

Participants

Reactant 4

HCID 69962-Chlorobenzaldehyde

HCID 16275Cyclohexanecarboxaldehyde

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

HCID 18405381HCID 18405381, compound

Product 2

HCID 57043039HCID 57043039, compound

HCID 69686185HCID 69686185, compound

Procedure

5-(Adamantan-1-yloxymethyl)-2-(2-chloro-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-chloro-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-chloro-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-chloro-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) 12.82 (2H, br s), 9.96 (1H, s), 8.51 (1H, s), 7.94 (1H, d), 7.73 (1H, dd), 7.61 (2H, m), 7.45 (3H, m), 4.90 (2H, s), 2.11 (3H, s), 1.79 (6H, s), 1.59 (6H, s). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan.

Sources & evidence

ORD record: ord-ce3a9c1e8b9d490da14688f551c4ac09
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479531B1

Reaction notes

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