Sodium Hydroxide → 3-(Methylsulfanyl)-5-[(pyridin-4-yl)amino]-1,2-thiazole-4-carboxamide
Reaction equation
[CH3:1][S:2][C:3]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[S:5][N:4]=1.[OH-:17].[Na+]>S(=O)(=O)(O)O>[CH3:1][S:2][C:3]1[C:7]([C:8]([NH2:9])=[O:17])=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[S:5][N:4]=1Participants
4
Procedure
Compound 7 (1.0 g, 4.0 mmol) is dissolved in sulfuric acid (5 mL). The resulting solution is stirred at room temperature for 2 hours, heated to 50° C. for 3.5 hours, then at room temperature for 18 hours, then heated to 50° C. for 1 hour. The reaction was then cooled to room temperature and 1N NaOH (5 mL) was added. The resulting solids were filtered and washed with saturated aqueous sodium bicarbonate to provide 8 (1.15 g, 4.0 mmol). 1H NMR (d6 DMSO): 5 8.12 (2H, d, J=5.8 Hz), 6.78 (2H, d, J=5.8 Hz), 2.32 (3H, s); LRMS (M+): 267.0, (M−): 265.0.