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【结 构 式】

【分子编号】48934

【品名】ethyl 4-[([2-[amino(imino)methyl]-1,2,3,4-tetrahydro-7-isoquinolinyl]oxy)methyl]-1-(4-pyridinyl)-4-piperidinecarboxylate

【CA登记号】

【 分 子 式 】C24H31N5O3

【 分 子 量 】437.54204

【元素组成】C 65.88% H 7.14% N 16.01% O 10.97%

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:(IX)

Treatment of protected hydroxy tetrahydroisoquinoline (I) with chloromethyl methyl sulfide (II) in DMF in the presence of NaH affords methylsulfanyl derivative (III), which is then converted into chloromethoxy compound (IV) by reaction with sulfuryl chloride in dichloromethane. Condensation of (IV) with piperidine derivative (V) by means of lithium diisopropylamide in THF provides compound (VI), whose Boc group is removed by means of TFA in CHCl3 to furnish deprotected tetrahydroisoquinolinic compound (VII). An amidinium group is then incorporated onto (VII) by reaction with 1H-pyrazole-1-carboxamidine hydrochloride (VIII) to give amidino derivative (IX), whose ethyl ester group is hydrolyzed by refluxing with HCl to afford carboxylic acid (X) as a dihydrochloride salt. Finally, the desired product is obtained by formation of the corresponding monomethanesulfonate trihydrate derivative by treatment with MsOH.

1 Hayashi, M.; Yokota, K.; Katoh, S. (Japan Tobacco Inc.); Amidine cpds.. EP 1070714; JP 2000136190; WO 9952895 .
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) 28635 tert-butyl 7-hydroxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate C14H19NO3 详情 详情
(II) 27701 chloro(methylsulfanyl)methane 2373-51-5 C2H5ClS 详情 详情
(III) 48929 tert-butyl 7-[(methylsulfanyl)methoxy]-3,4-dihydro-2(1H)-isoquinolinecarboxylate C16H23NO3S 详情 详情
(IV) 48930 tert-butyl 7-(chloromethoxy)-3,4-dihydro-2(1H)-isoquinolinecarboxylate C15H20ClNO3 详情 详情
(V) 44838 ethyl 1-(4-pyridinyl)-4-piperidinecarboxylate C13H18N2O2 详情 详情
(VI) 48931 tert-butyl 7-[[4-(ethoxycarbonyl)-1-(4-pyridinyl)-4-piperidinyl]methoxy]-3,4-dihydro-2(1H)-isoquinolinecarboxylate C28H37N3O5 详情 详情
(VII) 48932 ethyl 1-(4-pyridinyl)-4-[(1,2,3,4-tetrahydro-7-isoquinolinyloxy)methyl]-4-piperidinecarboxylate C23H29N3O3 详情 详情
(VIII) 48933 1H-pyrrole-1-carboximidamide C5H7N3 详情 详情
(IX) 48934 ethyl 4-[([2-[amino(imino)methyl]-1,2,3,4-tetrahydro-7-isoquinolinyl]oxy)methyl]-1-(4-pyridinyl)-4-piperidinecarboxylate C24H31N5O3 详情 详情
(X) 48935 4-[([2-[amino(imino)methyl]-1,2,3,4-tetrahydro-7-isoquinolinyl]oxy)methyl]-1-(4-pyridinyl)-4-piperidinecarboxylic acid C22H27N5O3 详情 详情
Extended Information