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

HRID 1018383Notes

Reaction equation

HRID 1018383 reaction equation
[CH:1]1([CH:8]=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:10]1(C=O)CCCC[CH2:11]1.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=C[CH:48]=[C:47]([NH2:51])C=1)C1C=CC=CC=1.[CH3:53][NH:54][CH2:55][C@@H:56]([C@H:58]([C@@H:60]([C@@H:62]([CH2:64]O)O)O)O)O.[OH2:66].O1[CH2:72][CH2:71][O:70][CH2:69]C1>O>[C:71]12([O:70][CH2:69][C:53]3[NH:54][C:55]([CH:56]4[CH2:58][CH2:60][CH2:62][CH2:64][CH2:11][CH2:10]4)=[N:51][C:47]=3[C:48]([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])[CH2:72][CH:6]3[CH2:5][CH:4]([CH2:2][CH:1]([CH2:7]3)[CH2:8]1)[CH2:3]2

Participants

8

Reactant 6

HCID 8567N-Methyl-D-glucamineHCID 16275CyclohexanecarboxaldehydeHCID 77961FormylcycloheptaneHCID 15428374Benzyl 3-aminobenzoateHCID 218864351,4-Dioxane--water (1/1)HCID 538373385-Amino-2-methyl-benzoic acid benzyl ester

Product 1

HCID 184054445-{[5-(Adamantan-1-yloxymethyl)-2-cycloheptyl-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 216, with the modification that cycloheptanecarboxaldehyde was used in step d instead of cyclohexanecarboxaldehyde and 5-amino-2-methyl-benzoic acid benzyl ester replaced 3-amino-benzoic acid benzyl ester in step f. 1H NMR (300 MHz, d6-DMSO) 12.40 (1H, br s), 12.11 (1H, br s), 9.55 (1H, s), 8.30 (1H, s), 7.76 (1H, d), 7.20 (1H, d), 4.78 (2H, s), 2.87 (1H, m), 2.45 (3H, s), 2.10-1.47 (27H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 60.38; H, 8.36; N, 7.51%; C37H56N4O9.2.0 H2O requires: C, 60.31; H, 8.21; N, 7.60%.

Sources & evidence

ORD record
ord-636bb3f110ac461a9ab4b58a177c137d
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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