N-Methyl-D-glucamine → HCID 86758605, compound

HRID 1018381Notes

Reaction equation

[C:1]12([O:11][CH2:12][C:13]3[NH:17][C:16]([CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[N:15][C:14]=3[C:24]([NH:26][C:27]3[CH:28]=[C:29]([CH2:33][C:34](O)=[O:35])[CH:30]=[CH:31][CH:32]=3)=[O:25])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C12(OCC3NC(C4CCCCC4)=[N:51]C=3C(NC3C=C(C=CC=3)C(O)=O)=O)CC3CC(CC(C3)C1)C2.CNC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[OH2:85].O1CCOCC1>>[OH:85][NH:51][C:34]([CH2:33][C:29]1[CH:28]=[C:27]([NH:26][C:24]([C:14]2[N:15]=[C:16]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[NH:17][C:13]=2[CH2:12][O:11][C:1]23[CH2:2][CH:3]4[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]4)[CH2:10]2)[CH2:8]3)=[O:25])[CH:32]=[CH:31][CH:30]=1)=[O:35]

Participants

Reactant 4

HCID 8567N-Methyl-D-glucamine

HCID 9832467HCID 9832467, compound

HCID 18405618HCID 18405618, compound

HCID 218864351,4-Dioxane--water (1/1)

Product 1

HCID 86758605HCID 86758605, compound

Procedure

The title compound was prepared according to the procedure of Example 286, with the modification that (3-{[5-(adamantan-1-yloxymethyl)-2-cyclohexyl-1H-imidazole-4-carbonyl]-amino}-phenyl)-acetic acid (Example 219) was used in step a instead of 3-{[5-(adamantan-1-yloxymethyl)-2-cyclohexyl -1H-imidazole-4-carbonyl]-amino}-benzoic acid. 1H NMR (300 MHz, d6-DMSO) 12.15 (1H, s), 10.62 (1H, s), 9.37 (1H, s), 8.80 (1H, s), 7.68 (1H, s), 7.58 (1H, d), 7.21 (1H, t), 6.94 (1H, d), 4.79 (2H, s), 3.25 (2H, s), 2.69 (1H, m), 2.11 (3H, br s), 1.90 (2H, m), 1.75 (8H, m), 1.55 (8H, m), 1.30 (4H, m). The hydroxamic acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 59.81; H, 8.06; N, 9.68%; C36H55N5O9.1.1H2O requires: C, 59.87; H, 7.99; N, 9.70%.

Sources & evidence

ORD record: ord-0c883d9e669e4c1db12c41d319842520
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479531B1

Reaction notes

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