Potassium Iodide → 4-{[({[3-(methylsulfanyl)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}-1,3-thiazol-2-amine

To a stirred suspension of N-hydroxy-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine (2.00 g, 6.90 mmol), in dry acetonitrile (115 mL) were added 4-(chloromethyl)-1,3-thiazol-2-amine (1.13 g, 7.59 mmol), cesium carbonate (4.72 g, 14.5 mmol) and potassium iodide (0.57 g, 3.45 mmol). The reaction mixture was stirred at room temperature for 26 h, then insolubles were removed by filtration and washed with dichloromethane (3×40 mL) and ethyl acetate (3×40 mL). The filtrates were combined and concentrated in vacuo. The residue was dissolved in dichloromethane (100 mL), washed with water (50 mL), the aqueous layer was extracted with dichloromethane (50 mL) and the combined organic layers were dried over MgSO4 and concentrated in vacuo to afford 4-{[({[3-(methylsulfanyl)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}-1,3-thiazol-2-amine [1.10 g, yield 42%; HPLC/MS: m/z=362 (M+H); logP(HCOOH)=1.76].

1. custominsolubles were removed by filtration
2. washwashed with dichloromethane (3×40 mL) and ethyl acetate (3×40 mL)
3. concentrationconcentrated in vacuo
4. dissolutionThe residue was dissolved in dichloromethane (100 mL)
5. washwashed with water (50 mL)
6. extractionthe aqueous layer was extracted with dichloromethane (50 mL)
7. dry with materialthe combined organic layers were dried over MgSO4
8. concentrationconcentrated in vacuo

ORD 기록

ord-d300f66efe734e3f93a6b5bc91f3ac76

출처 데이터셋

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08466176B2