• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】50250

【品名】3-[3-(dimethylamino)propyl]-4-[(E)-1-hydroxy-3-methyl-6-phenyl-5-hexenyl]-1,2,3-oxadiazol-3-ium-5-olate

【CA登记号】

【 分 子 式 】C20H29N3O3

【 分 子 量 】359.46868

【元素组成】C 66.83% H 8.13% N 11.69% O 13.35%

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:(VIII)

Alkylation of N,N-dimethyl-1,3-propanediamine (II) with ethyl bromoacetate (I) afforded the diamino ester (III). Basic hydrolysis of (III) and subsequent nitrosation of the resulting diamino acid (IV) yielded the nitrosamine (V). Cyclization of (V) in hot acetic anhydride as the dehydrating agent gave rise to sydnone (VI). Lithiation of (VI), followed by condensation with aldehyde (VII), produced adduct (VIII) as an inseparable mixture of diastereomers. The hydroxyl group of (VIII) was then protected as the methyl ether (IX) by alkylation with iodomethane and NaH. The azomethyne intermediate, generated by ejection of CO2 from (IX) upon heating in xylene, underwent an intramolecular 1,3-dipolar cycloaddition with the olefin double bond to furnish the indazole derivative (X). Finally, the target compound was obtained by aromatization of (X) under acidic conditions in the presence of platinum catalyst.

1 Yeu, J.P.; et al.; An expedient synthesis of 1-[3-(dimethylamino)propyl]-5-methyl-3-phenyl-1H-indazole (FS-32) - An antidepressant. Synthesis 2001, 12, 1775.
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) 16640 Ethyl 2-bromoacetate; Ethyl bromoacetate 105-36-2 C4H7BrO2 详情 详情
(II) 25248 N-(3-aminopropyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,3-propanediamine 109-55-7 C5H14N2 详情 详情
(III) 50245 ethyl 2-[[3-(dimethylamino)propyl]amino]acetate C9H20N2O2 详情 详情
(IV) 50246 2-[[3-(dimethylamino)propyl]amino]acetic acid C7H16N2O2 详情 详情
(V) 50247   C7H15N3O3 详情 详情
(VI) 50248 3-[3-(dimethylamino)propyl]-1,2,3-oxadiazol-3-ium-5-olate C7H13N3O2 详情 详情
(VII) 50249 (E)-3-methyl-6-phenyl-5-hexenal C13H16O 详情 详情
(VIII) 50250 3-[3-(dimethylamino)propyl]-4-[(E)-1-hydroxy-3-methyl-6-phenyl-5-hexenyl]-1,2,3-oxadiazol-3-ium-5-olate C20H29N3O3 详情 详情
(IX) 50251 3-[3-(dimethylamino)propyl]-4-[(E)-1-methoxy-3-methyl-6-phenyl-5-hexenyl]-1,2,3-oxadiazol-3-ium-5-olate C21H31N3O3 详情 详情
(X) 50252 3-(7-methoxy-5-methyl-3-phenyl-4,5,6,7-tetrahydro-1H-indazol-1-yl)-N,N-dimethyl-1-propanamine; N-[3-(7-methoxy-5-methyl-3-phenyl-4,5,6,7-tetrahydro-1H-indazol-1-yl)propyl]-N,N-dimethylamine C20H29N3O 详情 详情
Extended Information