benzyl [4-(azidomethyl)phenyl](imino)methylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】50385

【品名】benzyl [4-(azidomethyl)phenyl](imino)methylcarbamate

【CA登记号】

【分子式】C₁₆H₁₅N₅O₂

【分子量】309.3276

【元素组成】C 62.13% H 4.89% N 22.64% O 10.34%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IV)

The reaction of 4-cyanobenzyl bromide (I) with NaN3 in DMF gives 4-cyanobenzyl azide (II), which is treated first with HCl and then with ammonia to yield 4-(azidomethyl)benzamidine (III). Protection of the amidino group of (III) with benzyl chloroformate affords the protected compound (IV), which is finally reduced at the azido group with PPh3 in THF to provide 4-(benzyloxycarbonylamidino)benzylamine (V).

参考文献中间体

合成目标

【1】 Bayes, M.; Silvestre, J.S.; Sorbera, L.A.; Castaner, J.; Melagatran and Ximelagatran. Drugs Fut 2001, 26, 12, 1155.
【2】 Antonsson, K.T.; Bylund, R.E.; Gustafsson, N.D.; Nilsson, N.O.I. (AstraZeneca plc); New peptide derivs.. EP 0701568; JP 1996511018; JP 2001322974; US 5602253; US 5723444; WO 9429336 .

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)	14200	4-(Bromomethyl)benzonitrile; alpha-Bromo-p-tolunitrile	17201-43-3	C₈H₆BrN	详情	详情
(II)	50383	4-(azidomethyl)benzonitrile		C₈H₆N₄	详情	详情
(III)	50384	4-(azidomethyl)benzenecarboximidamide		C₈H₉N₅	详情	详情
(IV)	50385	benzyl [4-(azidomethyl)phenyl](imino)methylcarbamate		C₁₆H₁₅N₅O₂	详情	详情
(V)	50386	benzyl [4-(aminomethyl)phenyl](imino)methylcarbamate		C₁₆H₁₇N₃O₂	详情	详情

Extended Information