N-(3-[[(aminocarbonyl)amino]carbonyl]phenyl)-2,2,2-trifluoroacetamide -Drug Synthesis Database

【结构式】

【分子编号】26641

【品名】N-(3-[[(aminocarbonyl)amino]carbonyl]phenyl)-2,2,2-trifluoroacetamide

【CA登记号】

【分子式】C₁₀H₈F₃N₃O₃

【分子量】275.1871496

【元素组成】C 43.65% H 2.93% F 20.71% N 15.27% O 17.44%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

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.

参考文献中间体

合成目标

【1】 Bekesi, J.G.; Holland, J.F.; Jiang, J.-D.; Ma, L.; Roboz, J.; Deng, L.; Weisz, I.; Synthesis, cancericidal and antimicrotubule activities of 3-(haloacetamido)-benzoylureas. Anti-Cancer Drug Des 1998, 13, 7, 735.

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)	26638	3-Aminobenzoic acid	99-05-8	C₇H₇NO₂	详情	详情
(II)	26639	3-[(2,2,2-trifluoroacetyl)amino]benzoic acid		C₉H₆F₃NO₃	详情	详情
(III)	26640	3-[(2,2,2-trifluoroacetyl)amino]benzoyl chloride		C₉H₅ClF₃NO₂	详情	详情
(IV)	19310	urea	57-13-6	CH₄N₂O	详情	详情
(V)	26641	N-(3-[[(aminocarbonyl)amino]carbonyl]phenyl)-2,2,2-trifluoroacetamide		C₁₀H₈F₃N₃O₃	详情	详情
(VI)	26642	N-(3-aminobenzoyl)urea		C₈H₉N₃O₂	详情	详情
(VII)	11296	2-Chloroacetyl chloride; Chloroacetic chloride	79-04-9	C₂H₂Cl₂O	详情	详情
(VIII)	26643	N-(3-[[(aminocarbonyl)amino]carbonyl]phenyl)-2-chloroacetamide		C₁₀H₁₀ClN₃O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

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.

参考文献中间体

合成目标

【1】 Bekesi, J.G.; Holland, J.F.; Jiang, J.-D.; Ma, L.; Roboz, J.; Deng, L.; Weisz, I.; Synthesis, cancericidal and antimicrotubule activities of 3-(haloacetamido)-benzoylureas. Anti-Cancer Drug Des 1998, 13, 7, 735.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	14005	2-Bromoacetyl bromide; Bromoacetyl bromide	598-21-0	C₂H₂Br₂O	详情	详情
	19310	urea	57-13-6	CH₄N₂O	详情	详情
(I)	26638	3-Aminobenzoic acid	99-05-8	C₇H₇NO₂	详情	详情
(II)	26639	3-[(2,2,2-trifluoroacetyl)amino]benzoic acid		C₉H₆F₃NO₃	详情	详情
(III)	26640	3-[(2,2,2-trifluoroacetyl)amino]benzoyl chloride		C₉H₅ClF₃NO₂	详情	详情
(IV)	26641	N-(3-[[(aminocarbonyl)amino]carbonyl]phenyl)-2,2,2-trifluoroacetamide		C₁₀H₈F₃N₃O₃	详情	详情
(V)	26642	N-(3-aminobenzoyl)urea		C₈H₉N₃O₂	详情	详情

Extended Information