反应详情

温度

70 °C

To a solution of methyl 4-{[(4-chlorobutyl)sulfonyl]amino}-1H-benzimidazole-6-carboxylate (D252) (1 g, 3.23 mmol, 1 equiv) in EtOH (50 ml) was added NEt3 (2 ml, excess) and the resulting solution was stirred at 70° C. for 2 days. then cooled to room temperature and concentrated in vacuo. The residue was dissolved in AcOEt and the organic phase was washed with a 5% aqueous citric acid solution. The aqueous phase was saturated with NaCl and extracted twice with AcOEt. The combined organic phases were dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (CH2Cl2/MeOH: 96/4 to 90/10) gave methyl 4-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-1H-benzimidazole-6-carboxylate (D253) (250 mg, 25%) as a pale yellow solid. [M+H]+=310.3, RT=2.11 min.

1. temperaturethen cooled to room temperature
2. concentrationconcentrated in vacuo
3. dissolutionThe residue was dissolved in AcOEt
4. washthe organic phase was washed with a 5% aqueous citric acid solution
5. extractionextracted twice with AcOEt
6. dry with materialThe combined organic phases were dried over MgSO4
7. concentrationconcentrated in vacuo
8. customPurification of the residue by flash chromatography on silica gel (CH2Cl2/MeOH: 96/4 to 90/10)