[CH2:1]([NH:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[S:8][C:7]=1[C:17]([O:19]C)=[O:18])[CH2:2][CH2:3][CH3:4].C[O-].[Na+].CO.Cl>O>[CH2:1]([NH:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[S:8][C:7]=1[C:17]([OH:19])=[O:18])[CH2:2][CH2:3][CH3:4]A mixture of methyl 3-(butylamino)-5-(pyridin-4-yl)thiophene-2-carboxylate (0.460 g, 1.58 mmol), sodium methoxide (0.257 g, 4.75 mmol), methanol (6.4 mL) and water (1.6 mL) was refluxed overnight. The mixture was cooled in an ice-bath and conc. HCl (0.390 mL, 4.75 mmol) was added. The resultant yellow precipitate was collected by filtration and washed with water and methanol to afford the title compound (0.370 g, 85%) as a yellow solid:
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