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【结 构 式】

【分子编号】65774

【品名】 

【CA登记号】 

【 分 子 式 】C16H20ClO2

【 分 子 量 】279.7863

【元素组成】C 68.69% H 7.21% Cl 12.67% O 11.44%

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:(XXV)

The building block (IX) can be obtained by several related methods:
Reaction of 4,4-dimethylcyclohexanone (XVII) with DMF and PBr3 under Vilsmeier formylation conditions provides the carbaldehyde (XVIII), which is subjected to reductive amination with 4-piperazinobenzoic acid ethyl ester (XIX) and NaBH3CN resulting in the cyclohexenylmethyl piperazine (XX). Subsequent Suzuki coupling of compound (XX) with 4-chlorophenylboronic acid (XXI) followed by ethyl ester hydrolysis of the resultant adduct (XXII) leads to the target intermediate (IX) (1). Scheme 3.
In a related procedure, 2-hydroxy-5,5-dimethyl-1-cyclohexenecarboxylic acid methyl ester (XXIII) is converted to the corresponding triflate (XXIV), which undergoes Suzuki coupling with boronic acid (XXI) to yield the 2-arylcyclohexenecarboxylate derivative (XXV). After reduction of ester (XXV) with LiBH4, the resulting primary alcohol (XXVI) is converted to the corresponding mesylate (XXVII) with methanesulfonyl chloride, and then condensed with the piperazine derivative (XIX) followed by ethyl ester hydrolysis to yield the key precursor (IX) (4). Scheme 3.

1 Bruncko, M., Ding, H., Elmore, S.W. et al. (Abbott Laboratories Inc.). Apoptosis promoters. EP 1888550, US 2007027135, US 7390799, WO 2007040650.
4 Song, X., Bruncko, M., Ding, H. et al. P2 site SAR development toward ABT-263, an orally bioavailable inhibitor of Bcl-2 family proteins. 235th ACS Natl Meet (April 6-10, New Orleans) 2008, Abst MEDI 78.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IX) 65759     C26H31ClN2O2 详情 详情
(XVII) 65767 4,4-Dimethylcyclohexanone; 4,4-Dimethyl-1-cyclohexanone 4255-62-3 C8H14O 详情 详情
(XVIII) 65768     C9H13BrO 详情 详情
(XIX) 65769 Ethyl 4-(1-piperazinyl)benzoate 80518-57-6 C13H18N2O2 详情 详情
(XX) 65770     C22H31BrN2O2 详情 详情
(XXI) 17575 4-chlorophenylboronic acid 1679-18-1 C6H6BClO2 详情 详情
(XXII) 65771     C28H35ClN2O2 详情 详情
(XXIII) 65772     C10H16O3 详情 详情
(XXIV) 65773     C11H16F3O5S 详情 详情
(XXV) 65774     C16H20ClO2 详情 详情
(XXVI) 65775     C15H19ClO 详情 详情
(XXVII) 65776     C16H21ClO3S 详情 详情
Extended Information