Benzaldehyde, (dimethylamino)- → HCID 18405397, compound

HRID 1018343Notes

Reaction equation

HRID 1018343 reaction equation
CC1(C)C2CC1CC=C2C=O.CN(C)[C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=[O:17].[C:23]12([CH2:33][CH2:34][C:35]3[NH:39][C:38]([C:40]4[CH:41]5[CH2:46][CH:43]([CH2:44][CH:45]=4)[C:42]5([CH3:48])[CH3:47])=[N:37][C:36]=3[C:49](O)=[O:50])[CH2:32][CH:27]3[CH2:28][CH:29]([CH2:31][CH:25]([CH2:26]3)[CH2:24]1)[CH2:30]2.Cl.C[O:54][C:55](=[O:63])[C:56]1[CH:61]=[CH:60][CH:59]=[C:58]([NH2:62])[CH:57]=1>>[CH2:16]([O:17][C:49]([C:36]1[N:37]=[C:38]([C:40]2[CH:41]3[CH2:46][CH:43]([CH2:44][CH:45]=2)[C:42]3([CH3:48])[CH3:47])[NH:39][C:35]=1[CH2:34][CH2:33][C:23]12[CH2:32][CH:27]3[CH2:28][CH:29]([CH2:31][CH:25]([CH2:26]3)[CH2:24]1)[CH2:30]2)=[O:50])[C:15]1[CH:14]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:23]12([CH2:33][CH2:34][C:35]3[NH:39][C:38]([C:40]4[CH:41]5[CH2:46][CH:43]([CH2:44][CH:45]=4)[C:42]5([CH3:48])[CH3:47])=[N:37][C:36]=3[C:49]([NH:62][C:58]3[CH:57]=[C:56]([CH:61]=[CH:60][CH:59]=3)[C:55]([OH:54])=[O:63])=[O:50])[CH2:32][CH:27]3[CH2:26][CH:25]([CH2:31][CH:29]([CH2:28]3)[CH2:30]1)[CH2:24]2

Participants

6

Reactant 4

HCID 34289Benzaldehyde, (dimethylamino)-HCID 611306,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-carboxaldehydeHCID 12238913Methyl 3-aminobenzoate hydrochlorideHCID 18405411HCID 18405411, compound

Product 2

HCID 18405397HCID 18405397, compoundHCID 69686212HCID 69686212, compound

Procedure

5-(2-Adamantan-1-yl-ethyl)-2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1H-imidazole-4-carboxylic acid benzyl ester was prepared according to the procedure of Example 70, step a, with the modification that (1R)-(−)-myrtenal was used in instead of 2-dimethylamino-benzaldehyde. The benzyl ester was hydrolysed according to the procedure of Example 20, step c and the resulting 5-(2-adamantan-1-yl-ethyl)-2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1H-imidazole-4-carboxylic acid was reacted with 3-amino-benzoic acid methyl ester hydrochloride using essentially the same procedure as in Example 52, step a. Deprotection was carried out following essentially the procedure of Example 36, step d to afford the title compound. 1H NMR (300 MHz, d4-MeOH) 8.36 (1H, t), 7.90 (1H, ddd), 7.75 (1H, dt), 7.42 (1H, t), 6.30 (1H, m), 3.02 (1H, dt), 2.99 (2H, m), 2.57 (1H, m), 2.49 (2H, dd), 2.19 (1H, m), 1.95 (3H, s), 1.71 (6H, m), 1.60 (6H, d), 1.42 (2H, m), 1.40 (3H, s), 1.26 (1H, d), 0.90 (3H, s) was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 62.39; H, 7.98; N, 7.58%. C39H56N4O8.2.2 H2O requires: C, 62.55; H, 8.14; N, 7.48%.

Sources & evidence

ORD record
ord-ea53e743b38048d48939040f8231c0e8
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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