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【结 构 式】

【分子编号】16979

【品名】methyl (E)-3-[4-[(1Z,3E)-1-cyano-4-(3-pyridinyl)-1,3-butadienyl]phenyl]-2-propenoate

【CA登记号】

【 分 子 式 】C20H16N2O2

【 分 子 量 】316.35932

【元素组成】C 75.93% H 5.1% N 8.85% O 10.11%

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)

As shown in Scheme 22341901a, TER-930180 was prepared from 3-(3-pyridyl)acrolein (I) and methyl 4-(cyanomethyl)cinnamate (II). The condensation of (I) and (II) with sodium methoxide yielded a mixture of diene isomers (III), which was then hydrogenated over Pd/C in dioxane, and then over Raney Nickel at 10 approx. 15 atm of H2 in ammoniac/methanol. The amine thus obtained (IV) was treated with 4-chlorobenzenesulfonyl chloride, followed by hydrolyzation with sodium hydroxide solution, yielding TER-930180. The starting materials (I) and (II) were obtained as follows: Reduction of methyl 3-(3-pyridyl)acrylate with DIBAL, and oxidation with manganese dioxide to yield 3-(3-pyridyl)acrolein (I). Bromination of methyl 4-methylcinnamate with NBS, and cyanization with potassium cyanide in the presence of PTC produced methyl 4-cyanomethylcinnamate (II).

1 Kasukawa, H.; Ohnishi, H.; TER-930180. Drugs Fut 1996, 21, 1, 33.
2 Ohnishi, H.; Miyakoshi, M.; Isozaki, M.; Fujitake, M.; Mikami, N.; Yanoshita, R.; Akasofu, H.; Sugizaki, K.; Nakata, N. (Terumo Corp.); N-(3-Pyridylalkyl)sulfonamide deriv. and pharmaceutical preparation containing thereof. EP 0501876; JP 1992270265; JP 1993043546; JP 1993043547; US 5374641 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
15787 4-chlorobenzenesulfonyl chloride;4-chlorobenzene-1-sulfonyl chloride 98-60-2 C6H4Cl2O2S 详情 详情
(I) 16977 (E)-3-(3-pyridinyl)-2-propenal C8H7NO 详情 详情
(II) 16978 methyl (E)-3-[4-(cyanomethyl)phenyl]-2-propenoate C12H11NO2 详情 详情
(III) 16979 methyl (E)-3-[4-[(1Z,3E)-1-cyano-4-(3-pyridinyl)-1,3-butadienyl]phenyl]-2-propenoate C20H16N2O2 详情 详情
(IV) 16980 methyl 3-[4-[1-cyano-4-(3-pyridinyl)butyl]phenyl]propanoate C20H22N2O2 详情 详情
(V) 16981 methyl 3-[4-[1-(aminomethyl)-4-(3-pyridinyl)butyl]phenyl]propanoate C20H26N2O2 详情 详情
Extended Information