SM-8849, -Drug Synthesis Database

【结构式】

【药物名称】SM-8849

【化学名称】4-[1-(2-Fluorobiphenyl-4-yl)ethyl]-N-methylthiazole-2-amine
　　　　　　4-[1-(2-Fluorobiphenyl-4-yl)ethyl]-2-(methylamino)thiazole

【CA登记号】113759-19-6

【分子式】C₁₈H₁₇FN₂S

【分子量】312.41199

【开发单位】Sumitomo Pharmaceuticals (Originator)

【药理作用】Antiarthritic Drugs, IMMUNOMODULATING AGENTS, Immunosuppressants, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES

合成路线1

The reaction of 2-(2-fluorobiphenyl-4-yl)propionic acid (I) with thionyl chloride followed by treatment with tris (trimethylsilyloxy)ethylene gives 3-(2-fluorobiphenyl-4-yl)-1-hydroxy-2-butanone (II), which upon treatment with carbon tetrachloride and triphenylphosphine affords 1-chloro-3-(2-fluorobiphenyl-4-yl)-2-butanone (III). Finally, compound (III) is heated with N-methylthiourea in water.

参考文献中间体

【1】 Ozato, Y.; Tamura, N.; Masumori, H.; Yamamoto, M.; Kojima, A.; Nishikakau, F.; Kimura, Y. (Sumitomo Pharmaceuticals Co., Ltd.); Aminazole derivatives and their production and use. EP 0248399; JP 1988152368; JP 1993247014; US 4914112; US 5066666; US 5180731 .
【2】 Prous, J.; Castaner, J.; Graul, A.; SM-8849. Drugs Fut 1994, 19, 4, 347.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	12280	Flurbiprofen; 2-(2-Fluoro[1,1'-biphenyl]-4-yl)propionic acid	5104-49-4	C₁₅H₁₃FO₂	详情	详情
(II)	63470	3-(2-fluoro[1,1'-biphenyl]-4-yl)-1-hydroxy-2-butanone		C₁₆H₁₅FO₂	详情	详情
(III)	12663	1-Chloro-3-(2-fluoro[1,1'-biphenyl]-4-yl)-2-butanone		C₁₆H₁₄ClFO	详情	详情

Extended Information