Reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]2[NH:16][C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[N:31]=3)=[C:18]([C:20]3[CH:21]=[C:22]4[C:27](=[CH:28][CH:29]=3)[N:26]=[CH:25][CH:24]=[CH:23]4)[N:19]=2)=[CH:10][C:3]=1[O:4][CH2:5][C:6]([O:8]C)=[O:7].[OH-].[Na+].O>C(O)(=O)C>[F:1][C:2]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]2[NH:16][C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[N:31]=3)=[C:18]([C:20]3[CH:21]=[C:22]4[C:27](=[CH:28][CH:29]=3)[N:26]=[CH:25][CH:24]=[CH:23]4)[N:19]=2)=[CH:10][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of methyl 2-(2-fluoro-5-((5-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-imidazol-2-yl)methyl)phenoxy)acetate (Example 93) (47.5 mg, 0.098 mmol) was added aqueous NaOH solution (6 mg, 0.148 mmol, H2O (0.3 mL)). The reaction mixture was stirred for 1 hour, then diluted H2O (3 mL), and neutralized by addition of acetic acid to pH 7. The precipitate was filtered, washed with water, and dried under vacuum for overnight to afford the title compound (42.6 mg, 93%). (300 MHz, CDCl3+CD3OD) δ 2.57 (3H, s), 4.04 (N—H, 1H, bs), 4.75 (N—H, 1H, bs), 6.86 (1H, bs), 7.11 (2H, d), 7.23 (1H, d), 7.46-7.53 (2H, m), 7.85 (1H, dd), 8.05 (1H, d), 8.20 (1H, bs), 8.25 (1H, d), 8.87 (1H, dd). MS (EST) m/z 469 (MH+).
Workup
- filtrationThe precipitate was filtered
- washwashed with water
- customdried under vacuum for overnight
Sources & evidence
- ORD record
- ord-8ba84568e0854435b571850d1872449c
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410146B2
Linked notes
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