N-(4-amino-3-methoxyphenyl)methanesulfonamide -Drug Synthesis Database

【结构式】

【分子编号】30496

【品名】N-(4-amino-3-methoxyphenyl)methanesulfonamide

【CA登记号】

【分子式】C₈H₁₂N₂O₃S

【分子量】216.26096

【元素组成】C 44.43% H 5.59% N 12.95% O 22.19% S 14.83%

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：(VII)

2-Iodoisophthalic acid (II) is reacted with o-toluidine (I) to give 2-N-(2-methylphenyl)aminoisophthalic acid (III). Cyclization with concentrated H2SO4 provides the 5-methyl-9-oxoacridan-4-carboxylic acid (IV). Conversion of this compound to 5-methyl-9-chloroacridine-4-carbonyl chloride (V) and subsequent selective reaction first with methylamine to provide the methylcarboxamide (VI) and secondly with 4-amino-3-methoxymethanesulfonanilide (VII) gives the hydrochloride salt (VIII) of the desired compound. Conversion via the free base to the isethionate salt provides CI-921.

参考文献中间体

合成目标

【1】 Baguley, B.C.; Denny, W.A.; Finlay, G.J.; Wilson, W.R.; Twigden, S.J.; Atwell, G.J.; Rewcastle, G.W.; Synthesis and antitumour activity and DNA binding properties of a new derivative of amsacrine N,5-dimethyl-9-[(2-methoxy-4-methylsulfonylamino)phenylamino]-4-acridine carboxamide. Cancer Res 1984.
【2】 Denny, W.A.; Baguley, B.C.; Atwell, G.J.; Potential antitumor agents. 40. Orally active 4,5-disubstituted derivatives of amsacrine. J Med Chem 1984, 27, 3, 363-366.
【3】 Denny, W.A.; Atwell, G.J.; Baguley, B.C.; CI-921. Drugs Fut 1984, 9, 8, 575.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	13359	2-Hydroxy-1-ethanesulfonic acid	107-36-8	C₂H₆O₄S	详情	详情
(I)	15511	o-toluidine; 2-methylphenylamine;2-Methylaniline；2-Aminotoluene;1-Amino-2-methylbenzene;1-Methyl-2-aminobenzene; ortho-Toluidine	95-53-4	C₇H₉N	详情	详情
(II)	30491	2-Iodoisophthalic acid		C₈H₅IO₄	详情	详情
(III)	30492	2-(2-toluidino)isophthalic acid		C₁₅H₁₃NO₄	详情	详情
(IV)	30493	5-methyl-9-oxo-9,10-dihydro-4-acridinecarboxylic acid		C₁₅H₁₁NO₃	详情	详情
(V)	30494	9-chloro-5-methyl-4-acridinecarbonyl chloride		C₁₅H₉Cl₂NO	详情	详情
(VI)	30495	9-chloro-N,5-dimethyl-4-acridinecarboxamide		C₁₆H₁₃ClN₂O	详情	详情
(VII)	30496	N-(4-amino-3-methoxyphenyl)methanesulfonamide		C₈H₁₂N₂O₃S	详情	详情
(VIII)	30497	9-[2-methoxy-4-[(methylsulfonyl)amino]anilino]-4-methyl-5-[(methylamino)carbonyl]acridinium chloride		C₂₄H₂₅ClN₄O₄S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The reaction of 4-nitro-m-anisidine (I) with methanesulfonyl chloride in pyridine gives 4-nitromethanesulfony-m-anisidine (II), which is reduced with Fe and aqueous HCl yielding 4-aminomethanesulfony-m-anisidine (III) . Finally, this compound is condensed with 9-chloroacridine (IV).

参考文献中间体

合成目标

【1】 Denny, W.A.; et al.; Potential antitumor agents. 26. Anionic congeners of the 9-anilinoacridine. J Med Chem 1977, 21, 1, 5-10.
【2】 Cain, B.F.; et al.; Potential antitumor agents. 16. 4-(Acridin-9-ylamino)methanesulfonanilides. J Med Chem 1975, 18, 11, 1110-17.
【3】 Cain, B.F.; et al.; Potential antitumor agents. 23. 4'-(9-Acridinylamino)alkanesulfonanilide congeners bearing hydrophilic functionality. J Med Chem 1977, 20, 8, 987-996.
【4】 Paton, D.M.; Blancafort, P.; Serradell, M.N.; Castaner, J.; m-AMSA. Drugs Fut 1980, 5, 6, 277.

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)	32670	3-methoxy-4-nitroaniline; 3-methoxy-4-nitrophenylamine		C₇H₈N₂O₃	详情	详情
(II)	32671	N-(3-methoxy-4-nitrophenyl)methanesulfonamide		C₈H₁₀N₂O₅S	详情	详情
(III)	30496	N-(4-amino-3-methoxyphenyl)methanesulfonamide		C₈H₁₂N₂O₃S	详情	详情
(IV)	32672	9-chloroacridine	1207-69-8	C₁₃H₈ClN	详情	详情

Extended Information