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【结 构 式】

【分子编号】64954

【品名】1-[(4,6-dimethyl-5-pyrimidinyl)carbonyl]-4-piperidinone

【CA登记号】

【 分 子 式 】C12H15N3O2

【 分 子 量 】233.27012

【元素组成】C 61.79% H 6.48% N 18.01% O 13.72%

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:(VII)

The reaction of the chiral benzyl alcohol (I) with 4-chlorobenzenesulfonyl chloride (II) and DABCO in toluene gives the sulfonate (III), which is condensed with the monoprotected piperazine (IV) by means of K2CO3 in hot toluene/acetonitrile to yield the adduct (V). The deprotection of (V) by means of hot aqueous HCl affords the piperazine derivative (VI), which is condensed with the acyl piperidine (VII) --obtained by condensation of 4,6-dimethylpyrimidine-5-carboxylic acid (VIII) with 4-piperidone (IX) --by means of acetone cyanohydrin or NaCN/AcOH to provide the cyano adduct (X). Finally, this compound is treated with AlMe3 and Me-MgCl in THF/toluene to yield the target compound.

1 Gala, D.; Leong, W.; Jones, A.D.; Shi, X.; Chen, M.; D'sa, B.A.; Zhu, M.; Xiao, T.; Tang, S.; Goodman, A.J.; Nielsen, C.M.; Lee, G.M.; Gamboa, J.A. (Schering Corp.); Synthesis of piperidine and piperazine cpds. as CCR5 antagonists. WO 0384950 .
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) 64951 (1S)-2-methoxy-1-[4-(trifluoromethyl)phenyl]-1-ethanol C10H11F3O2 详情 详情
(II) 15787 4-chlorobenzenesulfonyl chloride;4-chlorobenzene-1-sulfonyl chloride 98-60-2 C6H4Cl2O2S 详情 详情
(III) 64952 (1S)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl 4-chlorobenzenesulfonate C16H14ClF3O4S 详情 详情
(IV) 50647 benzyl (3R)-3-methyl-1-piperazinecarboxylate C13H18N2O2 详情 详情
(V) 64953 benzyl (3S)-4-{(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl}-3-methyl-1-piperazinecarboxylate C23H27F3N2O3 详情 详情
(VI) 64946 2-methyl-1-{2-(methyloxy)-1-[4-(trifluoromethyl)phenyl]ethyl}piperazine; methyl 2-(2-methyl-1-piperazinyl)-2-[4-(trifluoromethyl)phenyl]ethyl ether C15H21F3N2O 详情 详情
(VII) 64954 1-[(4,6-dimethyl-5-pyrimidinyl)carbonyl]-4-piperidinone C12H15N3O2 详情 详情
(VIII) 64955 4,6-dimethyl-5-pyrimidinecarboxylic acid C7H8N2O2 详情 详情
(IX) 27115 4-piperidinone 40064-34-4 C5H9NO 详情 详情
(X) 64956 1-[(4,6-dimethyl-5-pyrimidinyl)carbonyl]-4-((3S)-4-{(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl}-3-methylpiperazinyl)-4-piperidinecarbonitrile C28H35F3N6O2 详情 详情
Extended Information