Methyl 5-amino-2-fluorobenzoate → 5-{[5-(2-adamantan-1-yl-ethyl)-2-(2,4,6-trimethyl-pyridine-3-yl)-1H-imidazole-4-carbonyl]-amino}-2-fluoro-benzoic acid methyl ester
Reaction equation
[C:1]12([CH2:11][CH2:12][C:13]3[NH:17][C:16]([C:18]4[C:19]([CH3:26])=[N:20][C:21]([CH3:25])=[CH:22][C:23]=4[CH3:24])=[N:15][C:14]=3[C:27](O)=[O:28])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:30][O:31][C:32](=[O:41])[C:33]1[CH:38]=[C:37]([NH2:39])[CH:36]=[CH:35][C:34]=1[F:40]>>[CH3:30][O:31][C:32](=[O:41])[C:33]1[CH:38]=[C:37]([NH:39][C:27]([C:14]2[N:15]=[C:16]([C:18]3[C:19]([CH3:26])=[N:20][C:21]([CH3:25])=[CH:22][C:23]=3[CH3:24])[NH:17][C:13]=2[CH2:12][CH2:11][C:1]23[CH2:10][CH:5]4[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]4)[CH2:8]2)[CH2:2]3)=[O:28])[CH:36]=[CH:35][C:34]=1[F:40]Participants
Reactant 2
Product 1
Procedure
5-(2-Adamantan-1-yl-ethyl)-2-(2,4,6-trimethyl-pyridine-3-yl)-1H-imidazole-4-carboxylic acid (Example 182) was reacted with 5-amino-2-fluoro-benzoic acid methyl ester according to the procedure of Example 20, step d to afford 5-{[5-(2-adamantan-1-yl-ethyl)-2-(2,4,6-trimethyl-pyridine-3-yl)-1H-imidazole-4-carbonyl]-amino}-2-fluoro-benzoic acid methyl ester. The ester was hydrolysed following the procedure of Example 36, step d, to afford the title compound as a white solid. 1H NMR (300 MHz, d6-DMSO) 12.50 (1H, br s), 9.67 (1H, s), 8.15 (1H, d), 7.71 (1H, m), 7.03 (2H, m), 2.99 (2H, m), 2.42 (3H, s), 2.25 (3H, s), 2.09 (3H, s), 1.92 (3H, br s), 1.60 (6H, m), 1.50 (6H, br s), 1.42 (2H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 53.44; H, 7.81; N, 8.03%. C38H52FN5O8.7.0 mols H2O requires: C, 53.57; H, 7.81; N, 8.22%.
Sources & evidence
- ORD record
- ord-37c7f11675c3471e9eafe4671d826072
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479531B1
Reaction notes
Loading…