Tetrahydrofuran → HCID 66749149, compound

Reaction equation

[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:12][C:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])=[C:14]([C:16]([O:18]C)=[O:17])[N:15]=2)[C:8]([CH3:27])=[CH:7][N:6]=1)(=[O:3])[CH3:2].C1COCC1.[OH-].[Na+]>CO>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:12][C:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])=[C:14]([C:16]([OH:18])=[O:17])[N:15]=2)[C:8]([CH3:27])=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Participants

Procedure

To a round bottom flask was added methyl 2-[2-(acetylamino)-5-methylpyridin-4-yl]-5-(2-chlorophenyl)-1,3-oxazole-4-carboxylate (2.30 g, 6.0 mmol), THF (20 mL), MeOH (30 mL), and 1M aqueous NaOH (25 mL). The reaction mixture was allowed to stir at rt overnight. The mixture was concentrated and 1M aqueous HCl was added until the solution became acidic. The mixture was filtered and the solid was dried to give 2-[2-(acetylamino)-5-methylpyridin-4-yl]-5-(2-chlorophenyl)-1,3-oxazole-4-carboxylic acid (Compound I-6) (1.4 g, 64%). LCMS (FA): m/z=372.2 (M+H).