Methyl 5-amino-2-fluorobenzoate → HCID 18405481, compound

HRID 1018357Notes

Reaction equation

HRID 1018357 reaction equation
[C:1]12([CH2:11][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](O)=[O:25])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C[O:28][C:29](=[O:38])[C:30]1[CH:35]=[C:34]([NH2:36])[CH:33]=[CH:32][C:31]=1[F:37]>>[C:1]12([CH2:11][CH2:12][C:13]3[NH:17][C:16]([CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]4)=[N:15][C:14]=3[C:24]([NH:36][C:34]3[CH:33]=[CH:32][C:31]([F:37])=[C:30]([CH:35]=3)[C:29]([OH:38])=[O:28])=[O:25])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

3

Reactant 2

HCID 15621043Methyl 5-amino-2-fluorobenzoateHCID 18405518HCID 18405518, compound

Product 1

HCID 18405481HCID 18405481, compound

Procedure

5-(2-Adamantan-1-yl-ethyl)-2-cyclohexyl-1H-imidazole-4-carboxylic acid (Example 252) was reacted with 5-amino-2-fluoro-benzoic acid methyl ester according to the procedure of Example 20, step d. The methyl ester was hydrolysed using the same procedure as in Example 36, step d to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 10.79 (1H, br s), 8.32 (1H, dd), 7.97 (1H, m), 7.32 (1H, m), 2.91 (3H, m), 1.98-1.34 (27H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 56.04; H, 8.48; N, 7.28%. C36H53FN4O8.4.5 mols H2O requires: C, 56.16; H, 8.12; N, 7.28%.

Sources & evidence

ORD record
ord-33489d6c32fb43878351a7862a02bfae
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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