3-Aminobenzoic acid -Drug Synthesis Database

【结构式】

【分子编号】26638

【品名】3-Aminobenzoic acid

【CA登记号】99-05-8

【分子式】C₇H₇NO₂

【分子量】137.13812

【元素组成】C 61.31% H 5.14% N 10.21% O 23.33%

与该中间体有关的原料药合成路线共 4 条

合成路线1 合成路线2 合成路线3 合成路线4

合成路线1

该中间体在本合成路线中的序号：(I)

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：(I)

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

合成路线3

该中间体在本合成路线中的序号：(IV)

The reaction of 3-nitro-1,8-naphthalic anhydride (I) with diethylenetriamine (II) in cool ethanol gives the cyclic monoamide (III). The reaction of the 3-nitro-1,8-naphthalic anhydride (I) with 3-aminobenzoic acid (IV) in hot DMSO/pyridine gives the corresponding cyclic naphthalamide (V). Finally, the benzoic acid (V) is condensed with the amine group of (III) by means of CDI in DMSO to afford the target bis naphthalamide.

参考文献中间体

合成目标

【1】 Suzuki, K.; Yamada, Y.; Asao, T.; Noguchi, K.; Wakida, M. (Taiho Pharmaceutical Co., Ltd.); Naphthalimidobenzamide derivs.. EP 1020446; US 6300331; WO 0001672 .

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)	15864	5-nitro-1H,3H-benzo[de]isochromene-1,3-dione; 3-Nitro-1,8-naphthalic anhydride	3027-38-1	C₁₂H₅NO₅	详情	详情
(II)	55379	2,2'-Diaminodiethylamine; 2,2'-Iminodiethylamine; Bis(beta-Aminoethyl)amine; Diethylentriamine; N-(2-Aminoethyl)-1,2-ethanediamine	111-40-0	C₄H₁₃N₃	详情	详情
(III)	55424	2-{2-[(2-aminoethyl)amino]ethyl}-5-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione		C₁₆H₁₆N₄O₄	详情	详情
(IV)	26638	3-Aminobenzoic acid	99-05-8	C₇H₇NO₂	详情	详情
(V)	55382	3-[5-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl]benzoic acid		C₁₉H₁₀N₂O₆	详情	详情

合成路线4

该中间体在本合成路线中的序号：(I)

The condensation of 3-aminobenzoic acid (I) with 3-nitro-1,8-naphthalic anhydride (II) in hot DMSO/pyridine gives the corresponding cyclic naphthalmide (III), which is condensed with diethylenetriamine (IV) by means of CDI in DMF to yield the benzamide (V). The reaction of (V) with CDI in DMF affords the imidazolylcarbonyl derivative (VI), which is condensed with 1-methylpiperazine (VII) in THF to provide the piperazinocarbonyl compound (VIII). Finally, the amino group of (VIII) is condensed with 3-nitro-1,8-naphthalic anhydride (II) in DMSO/pyridine to give the target bis-cyclic imide.

参考文献中间体

合成目标

【1】 Suzuki, K.; Yamada, Y.; Asao, T.; Noguchi, K.; Wakida, M. (Taiho Pharmaceutical Co., Ltd.); Naphthalimidobenzamide derivs.. EP 1020446; US 6300331; WO 0001672 .

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)	15864	5-nitro-1H,3H-benzo[de]isochromene-1,3-dione; 3-Nitro-1,8-naphthalic anhydride	3027-38-1	C₁₂H₅NO₅	详情	详情
(III)	55382	3-[5-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl]benzoic acid		C₁₉H₁₀N₂O₆	详情	详情
(IV)	55379	2,2'-Diaminodiethylamine; 2,2'-Iminodiethylamine; Bis(beta-Aminoethyl)amine; Diethylentriamine; N-(2-Aminoethyl)-1,2-ethanediamine	111-40-0	C₄H₁₃N₃	详情	详情
(V)	55383	N-{2-[(2-aminoethyl)amino]ethyl}-3-[5-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl]benzamide		C₂₃H₂₁N₅O₅	详情	详情
(VI)	55384	N-{2-[(2-aminoethyl)amino]ethyl}-3-(1H-imidazol-1-ylcarbonyl)-5-[5-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl]benzamide		C₂₇H₂₃N₇O₆	详情	详情
(VII)	10061	1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine	109-01-3	C₅H₁₂N₂	详情	详情
(VIII)	55385	N-{2-[(2-aminoethyl)amino]ethyl}-3-[(4-methyl-1-piperazinyl)carbonyl]-5-[5-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl]benzamide		C₂₉H₃₁N₇O₆	详情	详情

Extended Information