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【结 构 式】

【分子编号】37983

【品名】methyl 1-(2-ethoxy-2-oxoethyl)-4-oxo-3-piperidinecarboxylate

【CA登记号】

【 分 子 式 】C11H17NO5

【 分 子 量 】243.25972

【元素组成】C 54.31% H 7.04% N 5.76% O 32.89%

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:(II)

Alkylation of methyl 4-oxo-3-piperidinecarboxylate (I) with ethyl bromoacetate provided piperidineacetate (II). Subsequent decarbomethoxylation of (II) using LiCl in boiling DMF produced piperidone (III). On the other hand, coupling between 4-aminobenzonitrile (IV) and N-Boc-glycine (V) via activation with carbonyldiimidazole gave amide (V). The Boc group of (V) was then deprotected with HCl in EtOAc to yield 2-amino-N-(4-cyanophenyl)acetamide (VI). Reductive condensation of amine (VI) with piperidone (III) employing NaBH(OAc)3 furnished adduct (VII), which was further reductocondensed with chloroacetaldehyde to give chloroethyl amine (VIII). Cyclization of (VIII) in the presence of NaH generated piperazinone (IX). Finally, addition of hydroxylamine to the cyano group of (IX) provided the corresponding hydroxyamidine.

1 Suzuki, K.; Tsukamoto, S.; Yanagisawa, I.; Matsumoto, Y.; Ichihara, M.; Akamatsu, S.; Kaku, S.; Kawasaki, T.; Novel orally active GPIIb/IIIa antagonists: Synthesis and structure-activity relationship studies of oxopiperazine derivatives. Symp Med Chem 1999, Abst 1P-02.
2 Matsumoto, Y.; Akamatsu, S.; Ichihara, M.; Kawasaki, T.; Kaku, S.; Yanagisawa, I. (Merck Patent GmbH; Yamanouchi Pharmaceutical Co., Ltd.); Substd. amidinobenzene derivs. and medicinal compsns. thereof. EP 0905129; US 6057324; WO 9745413 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
16640 Ethyl 2-bromoacetate; Ethyl bromoacetate 105-36-2 C4H7BrO2 详情 详情
18066 N-alpha-t-BOC-glycine; 2-[(tert-butoxycarbonyl)amino]acetic acid 4530-20-5 C7H13NO4 详情 详情
(I) 28106 methyl 4-oxo-3-piperidinecarboxylate 56026-52-9 C7H11NO3 详情 详情
(II) 37983 methyl 1-(2-ethoxy-2-oxoethyl)-4-oxo-3-piperidinecarboxylate C11H17NO5 详情 详情
(III) 37984 ethyl 2-(4-oxo-1-piperidinyl)acetate C9H15NO3 详情 详情
(IV) 15361 4-Aminobenzonitrile 873-74-5 C7H6N2 详情 详情
(V) 37985 tert-butyl 2-(4-cyanoanilino)-2-oxoethylcarbamate C14H17N3O3 详情 详情
(VI) 37986 2-amino-N-(4-cyanophenyl)acetamide C9H9N3O 详情 详情
(VII) 37988 ethyl 2-(4-[[2-(4-cyanoanilino)-2-oxoethyl]amino]-1-piperidinyl)acetate C18H24N4O3 详情 详情
(VIII) 37987 ethyl 2-(4-[(2-chloroethyl)[2-(4-cyanoanilino)-2-oxoethyl]amino]-1-piperidinyl)acetate C20H27ClN4O3 详情 详情
(IX) 37989 ethyl 2-[4-[4-(4-cyanophenyl)-3-oxo-1-piperazinyl]-1-piperidinyl]acetate C20H26N4O3 详情 详情
Extended Information