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【结 构 式】

【分子编号】31728

【品名】6-[(2-azidoethoxy)methyl]-5-(tert-butoxycarbonyl)-2-ethyl-4-(4-nitrophenyl)-1,4-dihydro-3-pyridinecarboxylic acid

【CA登记号】

【 分 子 式 】C22H27N5O7

【 分 子 量 】473.48588

【元素组成】C 55.81% H 5.75% N 14.79% O 23.65%

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)

Hantzsch condensation of the (azidoethoxy)ketoester (I) with the benzylidene ketoester (II) formed the protected dihydropyridine (III). Selective deprotection of the cyanoethyl ester under basic conditions provided carboxylic acid (IV), which was further converted to amide (V). Then, acid cleavage of the tert-butyl ester gave acid (VI). Coupling with the (aminopropyl)piperidine (VII) furnished the corresponding amide (VIII). Finally, the azido group was reduced to the target amine by means of trimethyl phosphine.

1 Tyring, S.K.; Vander Straten, M.; Carrasco, D.; Tetrahedron Lett 1998, 39, 30, 5293-96.
2 Hong, X.; Nagarathnam, D.; Marzbadi, M.R.; et al.; Design and synthesis of novel dihydropyridine alpha-1A antagonists. Bioorg Med Chem Lett 1999, 9, 19, 2843.
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) 31725 tert-butyl 4-(2-azidoethoxy)-3-oxobutanoate C10H17N3O4 详情 详情
(II) 31726 2-cyanoethyl (Z)-3-(4-nitrophenyl)-2-propionyl-2-propenoate C15H14N2O5 详情 详情
(III) 31727 3-(tert-butyl) 5-(2-cyanoethyl) 2-[(2-azidoethoxy)methyl]-6-ethyl-4-(4-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate C25H30N6O7 详情 详情
(IV) 31728 6-[(2-azidoethoxy)methyl]-5-(tert-butoxycarbonyl)-2-ethyl-4-(4-nitrophenyl)-1,4-dihydro-3-pyridinecarboxylic acid C22H27N5O7 详情 详情
(V) 31729 tert-butyl 5-(aminocarbonyl)-2-[(2-azidoethoxy)methyl]-6-ethyl-4-(4-nitrophenyl)-1,4-dihydro-3-pyridinecarboxylate C22H28N6O6 详情 详情
(VI) 31730 5-(aminocarbonyl)-2-[(2-azidoethoxy)methyl]-6-ethyl-4-(4-nitrophenyl)-1,4-dihydro-3-pyridinecarboxylic acid C18H20N6O6 详情 详情
(VII) 18182 3-(4,4-diphenyl-1-piperidinyl)-1-propanamine; 3-(4,4-diphenyl-1-piperidinyl)propylamine C20H26N2 详情 详情
(VIII) 31731 2-[(2-azidoethoxy)methyl]-N(3)-[3-(4,4-diphenyl-1-piperidinyl)propyl]-6-ethyl-4-(4-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxamide C38H44N8O5 详情 详情
Extended Information