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【结 构 式】

【分子编号】48049

【品名】N-[(E)-4-(5-ethoxy-3-pyridinyl)-3-butenyl]-N-methylamine; (E)-4-(5-ethoxy-3-pyridinyl)-N-methyl-3-buten-1-amine

【CA登记号】

【 分 子 式 】C12H18N2O

【 分 子 量 】206.2878

【元素组成】C 69.87% H 8.79% N 13.58% O 7.76%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(VI)

Reaction of 3,5-dibromopyridine (I) with sodium ethoxide gave 3-bromo-5-ethoxypyridine (II). Palladium-catalyzed coupling of bromopyridine (II) with 3-buten-1-ol (III) yielded the pyridinylbutenol (IV), which was further converted to tosylate (V). Displacement of the tosylate group of (V) with methylamine then gave amine (VI).

1 Caldwell, W.S.; Dull, G.M.; Miller, C.H.; [3-(5-Ethoxypyridin)yl]-alkenyl 1 amine cpds.. US 5616716 .
2 Dull, G.M.; Dobson, G.P.; Caldwell, W.S. (R.J. Reynolds Tobacco Co.); Pharmaceutical compsns. for prevention and treatment of central nervous system disorders. WO 9740011 .
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) 48045 3,5-dibromopyridine 625-92-3 C5H3Br2N 详情 详情
(II) 48046 3-bromo-5-ethoxypyridine; 5-bromo-3-pyridinyl ethyl ether C7H8BrNO 详情 详情
(III) 19743 3-buten-1-ol 627-27-0 C4H8O 详情 详情
(IV) 48047 (E)-4-(5-ethoxy-3-pyridinyl)-3-buten-1-ol C11H15NO2 详情 详情
(V) 48048 (E)-4-(5-ethoxy-3-pyridinyl)-3-butenyl 4-methylbenzenesulfonate C18H21NO4S 详情 详情
(VI) 48049 N-[(E)-4-(5-ethoxy-3-pyridinyl)-3-butenyl]-N-methylamine; (E)-4-(5-ethoxy-3-pyridinyl)-N-methyl-3-buten-1-amine C12H18N2O 详情 详情

合成路线2

该中间体在本合成路线中的序号:(VI)

In a related method, 4-bromo-1-butene (VII) was reacted with methylamine to produce the secondary amine (VIII). After protection of (VIII) as the tert-butyl carbamate (IX), palladium-catalyzed coupling with 3-bromo-5-ethoxypyridine (II) furnished adduct (X). The N-Boc protecting group of (X) was then cleaved under acidic conditions to afford amine precursor (VI). The title hemigalactarate salt was finally prepared by treatment of amine (VI) with D-galactaric acid in aqueous ethanol.

1 Bane, A.J.; Dull, G.M.; Bencherif, M.; Miller, C.H.; Gatto, G.J.; TC-2559: A novel orally active ligand selective at neuronal acetylcholine receptors. Eur J Pharmacol 2000, 409, 1, 45.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(II) 48046 3-bromo-5-ethoxypyridine; 5-bromo-3-pyridinyl ethyl ether C7H8BrNO 详情 详情
(VI) 48049 N-[(E)-4-(5-ethoxy-3-pyridinyl)-3-butenyl]-N-methylamine; (E)-4-(5-ethoxy-3-pyridinyl)-N-methyl-3-buten-1-amine C12H18N2O 详情 详情
(VII) 11720 4-Bromo-1-butene 5162-44-7 C4H7Br 详情 详情
(VIII) 48050 N-(3-butenyl)-N-methylamine; N-methyl-3-buten-1-amine C5H11N 详情 详情
(IX) 48051 tert-butyl 3-butenyl(methyl)carbamate C10H19NO2 详情 详情
(X) 48052 tert-butyl (E)-4-(5-ethoxy-3-pyridinyl)-3-butenyl(methyl)carbamate C17H26N2O3 详情 详情
Extended Information