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【结 构 式】

【分子编号】15053

【品名】3-amino-5-ethyl-6-methyl-2(1H)-pyridinone

【CA登记号】

【 分 子 式 】C8H12N2O

【 分 子 量 】152.19616

【元素组成】C 63.13% H 7.95% N 18.41% O 10.51%

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:(VI)

L-697,661 was prepared via a convergent route: Formylation of 2-pentanone (I) with ethyl formate and sodium methoxide gave the ketoaldehyde sodium salt (II). When a mixture of anhydrous diethyl ether and absolute ethanol, 6:1 v/v, was used as solvent, the desired regioisomer precipitated out of solution. Treatment of ethyl nitroacetate (III) with ethanol saturated with ammonia provided nitroacetamide ammonium salt (IV). The nitroacetamide was then condensed with (II) in an aqueous solution of piperidinium acetate to afford the 3-nitropyridinone (V). Catalytic reduction of (V) provided the 3-aminopyridinone (VI). Treatment of chloroacetonitrile (VII) with hydrogen chloride and absolute ethanol gave ethyl chloroiminoacetate hydrochloride (VIII). Nitration of 2,4-dichlorophenol (IX), followed by catalytic reduction of the resultant product, led to the aminophenol (X). Coupling of (X) with (VIII) yielded the chloromethylbenzoxazole (XI), which was converted to the corresponding iodomethyl derivative (XII). Alkylation of the 3-aminopyridinone (VI) with the iodomethylbenzoxazole (XII) furnished L-697,661.

1 Saari, W.S.; Hoffman, J.M.; Wai, J.S.; et al.; 2-Pyridinone derivatives: A new class of nonnucleoside, HIV-1-specific reverse transcriptase inhibitors. J Med Chem 1991, 34, 9, 2922.
2 Goldmann, M.E.; Wai, J.S.; L-697,661. Drugs Fut 1992, 17, 4, 283.
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) 15048 2-pentanone 107-87-9 C5H10O 详情 详情
(II) 15049 sodium (Z)-2-ethyl-3-oxo-1-buten-1-olate C6H9NaO2 详情 详情
(III) 15050 ethyl 2-nitroacetate; Acetic acid, nitro-, ethyl ester 626-35-7 C4H7NO4 详情 详情
(IV) 15051 1-Carbamoyl-1-nitromethanide ammonium salt C2H7N3O3 详情 详情
(V) 15052 5-ethyl-6-methyl-3-nitro-2(1H)-pyridinone C8H10N2O3 详情 详情
(VI) 15053 3-amino-5-ethyl-6-methyl-2(1H)-pyridinone C8H12N2O 详情 详情
(VII) 14443 2-chloroacetonitrile; chloroacetonitrile 107-14-2 C2H2ClN 详情 详情
(VIII) 15055 1-chloro-2-pentanimine hydrochloride C5H11Cl2N 详情 详情
(IX) 11953 2,5-Dichlorophenol 583-78-8 C6H4Cl2O 详情 详情
(X) 15057 2-amino-3,6-dichlorophenol C6H5Cl2NO 详情 详情
(XI) 15058 4,7-dichloro-2-(chloromethyl)-1,3-benzoxazole C8H4Cl3NO 详情 详情
(XII) 15059 4,7-dichloro-2-(iodomethyl)-1,3-benzoxazole C8H4Cl2INO 详情 详情
Extended Information