MF-569, 3-IAABU

Chemical Name: N-[3-(Iodoacetamido)benzoyl]urea; N-Carbamoyl-3-(2-iodoacetamido)benzamide
CAS No. 218935-77-4
项目整合开发状态: Biological Testing
项目研究机构: Cytoskeleton (Originator), Mount Sinai School of Medicine (Originator), New York University (Originator)
合成路线:The acylation of 3-aminobenzoic acid with acetic anhydride in ethyl acetate gives the corresponding acetamide (II),which is treated with SOCl2 in refluxing ethyl acetate yielding 3-(trifluoroacetamido)benzoyl chloride (III).The reaction of (III) with urea (IV) in toluene at 100 C gives the acylated urea (V),which is deprotected with butylamine in refluxing methanol to afford N-(3-aminobenzoyl)urea (VI).The acylation of (VI) with chloroacetyl chloride (VII) in dimethylacetamide provides the corresponding amide (VIII),which is finally treated with NaI in dimethylacetamide.

合成路线:3-Aminobenzoic acid (I) was protected as the trifluoroacetamide (II) using trifluoroacetic anhydride and then converted to acid chloride (III) by means of SOCl2.Subsequent condensation of (III) with urea provided 3-(trifluoroacetamido)benzoylurea (IV).After cleavage of the trifluoroacetamido group of (IV) by treatment with methanolic n-butylamine,the deprotected aniline (V) was coupled with bromoacetyl bromide in DMA to furnish the title bromoacetamide.