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,C8H12ClNO,173.6439,5-(tert-butyl)-2-(chloromethyl)-1,3-oxaz

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摘 要:,C8H12ClNO,173.6439,5-(tert-butyl)-2-(chloromethyl)-1,3-oxazole
  • 【化学名】5-(tert-butyl)-2-(chloromethyl)-1,3-oxazole
  • 【CAS登记号】
  • 【结构式】,C8H12ClNO,173.6439,5-(tert-butyl)-2-(chloromethyl)-1,3-oxaz--药物合成数据库
  • 【分子式】C8H12ClNO
  • 【分子量】173.6439
  • 【来源】
  • 【合成情况】 
  • 〖目标产物〗BMS-419437
  • 〖合成路线〗
  • 〖合成方法〗Substitution of 1-bromo-3,3-dimethyl-2-butanone (I) with NaN3 affords the azido ketone (II), which is reduced to amino ketone (III) by either catalytic hydrogenation or with triphenylphosphine. Acylation of (III) with chloroacetyl chloride affords amide (IV). Cyclization of the keto amide (IV) in hot POCl3 or in the presence of Burgess' reagent leads to the chloromethyl oxazole (V). Displacement of the chlorine atom of (V) with thiourea provides the S-alkyl isothiourea (VI). Hydrolysis of (VI), followed by condensation with 2-amino-5-bromothiazole (VII) under phase-transfer conditions furnishes thioether (VIII). The amino thiazole (VIII) is then coupled with 4-(bromomethyl)phenylacetic acid (IX), yielding amide (X). Finally, the bromide group of (X) is displaced with 2-amino-1,3-propanediol (XI) to produce the title compound.
  • 〖参考〗Kim, K.S.; Misra, R.N.; Hunt, J.T.; Kimball, S.D.; Poss, M.A.; Han, W.-C.; Webster, K.R.; Cai, Z.-W.; Rawlins, D.B. (Bristol-Myers Squibb Co.); N-[5-[[[5-Alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl]-carboxamide inhibitors of cyclin dependent kinases. EP 124an>【CAS登记号】/span
 
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