4-(tert-butyl)benzylamine; [4-(tert-butyl)phenyl]methanamine -Drug Synthesis Database

【结构式】

【分子编号】47899

【品名】4-(tert-butyl)benzylamine; [4-(tert-butyl)phenyl]methanamine

【CA登记号】39895-55-1

【分子式】C₁₁H₁₇N

【分子量】163.26272

【元素组成】C 80.93% H 10.5% N 8.58%

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：(I)

Isocyanate (II) was prepared by treatment of 4-tert-butylbenzylamine (I) with phosgene in refluxing toluene. Subsequent coupling of isocyanate (II) with 4-(2-phthalimidoethoxy)-3-methoxybenzylamine (III) furnished urea (IV). The phthaloyl protecting group was then removed by hydrazinolysis. The resulting amine was finally converted to the corresponding hydrochloride salt.

参考文献中间体

合成目标

【1】 Campbell, E.A.; Walpole, C.S.J. (Novartis AG; Novartis Deutschland GmbH); Urea derivs. and their use as analgesics and antiinflammatory agents. WO 9711052 .

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)	47899	4-(tert-butyl)benzylamine; [4-(tert-butyl)phenyl]methanamine	39895-55-1	C₁₁H₁₇N	详情	详情
(II)	47900	1-(tert-butyl)-4-(isocyanatomethyl)benzene; 4-(tert-butyl)benzyl isocyanate		C₁₂H₁₅NO	详情	详情
(III)	47901	2-[2-[4-(aminomethyl)-2-methoxyphenoxy]ethyl]-1H-isoindole-1,3(2H)-dione		C₁₈H₁₈N₂O₄	详情	详情
(IV)	47902	N-[4-(tert-butyl)benzyl]-N'-[4-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethoxy]-3-methoxybenzyl]urea		C₃₀H₃₃N₃O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

Acylation of 2-fluoro-4-iodoaniline (I) with methanesulfonyl chloride affords the corresponding sulfonamide (II). Subsequent iodide displacement in (II) with zinc cyanide in the presence of palladium catalyst furnishes benzonitrile (III), which is further reduced to the benzylic amine (IV) by catalytic hydrogenation over Pd/C. Treatment of 4-(tert-butyl)benzylamine (V) with di-2-pyridyl thionocarbonate leads to the isothiocyanate (VI). This is finally condensed with amine (IV) to provide the target N,N'-dibenzyl thiourea derivative.

参考文献中间体

合成目标

【1】 Lee, J.W.; Kim, J.K.; Choi, J.K.; Lee, Y.S.; Park, H.G.; Kim, S.Y.; Kim, H.D.; Park, Y.H.; Suh, Y.G.; Joo, Y.H.; Lim, K.M.; Moh, J.H.; Jeong, Y.S.; Yi, J.B.; Oh, U.T.; Park, O.H.; Koh, H.J.; Oh, Y.M. (AmorePacific Corp.); Novel thiourea derivs. and the pharmaceutical compsns. containing the same. EP 1303483; EP 1311478; US 2003212140; WO 0216318; WO 0216319 .

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)	63342	2-fluoro-4-iodoaniline; 2-fluoro-4-iodophenylamine	29632-74-4	C₆H₅FIN	详情	详情
(II)	63343	N-(2-fluoro-4-iodophenyl)methanesulfonamide		C₇H₇FINO₂S	详情	详情
(III)	63344	N-(4-cyano-2-fluorophenyl)methanesulfonamide		C₈H₇FN₂O₂S	详情	详情
(IV)	63345	N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide		C₈H₁₁FN₂O₂S	详情	详情
(V)	47899	4-(tert-butyl)benzylamine; [4-(tert-butyl)phenyl]methanamine	39895-55-1	C₁₁H₁₇N	详情	详情
(VI)	63346	1-(1,1-dimethylethyl)-4-(isothiocyanatomethyl)benzene; [4-(1,1-dimethylethyl)phenyl]methyl isothiocyanate		C₁₂H₁₅NS	详情	详情

Extended Information