N-Methyl-D-glucamine → 5-{[5-(2-Adamantan-1-yl-ethyl)-2-tert-butyl-1H-imidazole-4-carbonyl]-amino}-2-methyl-benzoic Acid

HRID 1018344Notes

Reaction equation

HRID 1018344 reaction equation
[CH3:1][C:2]([CH3:6])([CH3:5])[CH:3]=O.C[N:8](C)[C:9]1C=CC=[CH:13][C:10]=1[CH:11]=O.C([O:25][C:26](=[O:35])[C:27]1[CH:32]=[C:31]([NH2:33])[CH:30]=[CH:29][C:28]=1[CH3:34])C1C=CC=CC=1.C(OC(=O)C1C=[CH:49][CH:48]=[C:47]([NH2:51])[CH:46]=1)C1C=CC=CC=1.CN[CH2:55][C@@H:56]([C@H:58]([C@@H:60]([C@@H:62]([CH2:64]O)O)O)O)O.[OH2:66].O1CCOC[CH2:68]1>O>[C:2]12([CH2:6][CH2:49][C:48]3[NH:8][C:9]([C:10]([CH3:13])([CH3:68])[CH3:11])=[N:46][C:47]=3[C:51]([NH:33][C:31]3[CH:30]=[CH:29][C:28]([CH3:34])=[C:27]([CH:32]=3)[C:26]([OH:25])=[O:35])=[O:66])[CH2:5][CH:62]3[CH2:60][CH:58]([CH2:56][CH:55]([CH2:64]3)[CH2:1]1)[CH2:3]2

Participants

8

Reactant 6

HCID 8567N-Methyl-D-glucamineHCID 12417PivalaldehydeHCID 34289Benzaldehyde, (dimethylamino)-HCID 15428374Benzyl 3-aminobenzoateHCID 218864351,4-Dioxane--water (1/1)HCID 538373385-Amino-2-methyl-benzoic acid benzyl ester

Product 1

HCID 184053955-{[5-(2-Adamantan-1-yl-ethyl)-2-tert-butyl-1H-imidazole-4-carbonyl]-amino}-2-methyl-benzoic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared according to the procedure of Example 70, with the modification that trimethylacetaldehyde was used in step a instead of 2-dimethylamino-benzaldehyde and 5-amino-2-methyl-benzoic acid benzyl ester replaced 3-amino-benzoic acid benzyl ester in step c. 1H NMR (300 MHz, d6-DMSO) 12.75 (1H, br s), 11.85 (1H, br s), 9.38 (1H, s), 8.25 (1H, s), 7.76 (1H, d), 7.21 (1H, d), 2.88 (2H, m), 2.45 (3H, s), 1.94 (3H, br s), 1.70-1.59 (6H, m), 1.510 (6H, br s), 1.34 (11H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 61.52; H, 8.39; N, 7.91%. C35H54N4O8.1.5 H2O requires: C, 61.29; H, 8.38; N, 8.17%.

Sources & evidence

ORD record
ord-1a177c320b9f44869fd22139a3e7f3cf
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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