ethyl 4-(3-amino-8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】63295

【品名】ethyl 4-(3-amino-8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylate

【CA登记号】

【分子式】C₂₂H₂₄ClN₃O₂

【分子量】397.90428

【元素组成】C 66.41% H 6.08% Cl 8.91% N 10.56% O 8.04%

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：(III)

The nitration of loratadine (I) (1) by means of tetrabutylammonium nitrate and trifluoroacetic anhydride (TFAA) in dichloromethane gives the 3-nitro derivative (II), which is reduced with iron filings and CaCl2 in refluxing ethanol/water to yield the 3-amino derivative (III). Treatment of compound (III) with NaNO2, HBr and Br2 provides 4-(3-bromo-8-chloro-5,6-dihydro-1H-benzo[5,6]-cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylic acid ethyl ester (IV) (see scheme 25468001a, intermediate (I).(2)

参考文献中间体

合成目标

【1】 Sorbera, L.A.; Castañer, J.; Lonafarnib. Drugs Fut 2003, 28, 12, 1168.
【2】 Structure-activity relationship of 3-substituted N-(pyridinylacetyl)-4-(8-chloro-5, 6-dihydro-11H-benzo[5,6]cyclohepta[1, 2-b]pyridin-11-ylidene)piperidine inhibitors of farnesyl-protein transferase: Design and synthesis of in vivo active antitumor compou. J Med Chem 1997, 40, 26, 4290.
【3】 Prous, J.; Castañer, J.; Loratadine. Drugs Fut 1987, 12, 6, 544.

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)	17877	ethyl 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylate	79794-75-5	C₂₂H₂₃ClN₂O₂	详情	详情
(II)	63294	ethyl 4-(8-chloro-3-nitro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylate		C₂₂H₂₂ClN₃O₄	详情	详情
(III)	63295	ethyl 4-(3-amino-8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylate		C₂₂H₂₄ClN₃O₂	详情	详情
(IV)	19338	ethyl 4-(3-bromo-8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylate		C₂₂H₂₂BrClN₂O₂	详情	详情

Extended Information