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【结 构 式】

【分子编号】64328

【品名】1-{[(2R,4R)-4-[(4-bromophenoxy)methyl]-2-(2,4-difluorophenyl)tetrahydro-2-furanyl]methyl}-1H-1,2,4-triazole; 4-bromophenyl [(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methyl ether

【CA登记号】

【 分 子 式 】C20H18BrF2N3O2

【 分 子 量 】450.2827464

【元素组成】C 53.35% H 4.03% Br 17.75% F 8.44% N 9.33% O 7.11%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(III)

The condensation of 4-chlorophenylsulfonate (I) with 4-bromophenol (II) by means of K2CO3 in hot DMF gives the aryl ether (III), which is condensed with piperazine (IV) by means of Pdo to yield the monosubstituted piperazine (V). Finally, this compound is condensed with the 4-bromophenyltriazolone (VI) by means of K2CO3 in hot DMSO to afford the target disubstituted piperazine

1 Hepperle, M.; Eckert, J.; Gala, D.; Shen, L.; Evans, C.A.; Goodman, A.; Mono N-arylation of piperazine(III): Metal-catalyzed N-arylation and its application to the novel preparations of the antifungal posaconazole and its advanced intermediate. Tetrahedron Lett 2002, 43, 18, 3359.
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) 17109 [(3S,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methyl 4-chlorobenzenesulfonate C20H18ClF2N3O4S 详情 详情
(II) 25313 4-bromophenol 106-41-2 C6H5BrO 详情 详情
(III) 64328 1-{[(2R,4R)-4-[(4-bromophenoxy)methyl]-2-(2,4-difluorophenyl)tetrahydro-2-furanyl]methyl}-1H-1,2,4-triazole; 4-bromophenyl [(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methyl ether C20H18BrF2N3O2 详情 详情
(IV) 10355 Diethylenediamine; Piperazine 110-85-0 C4H10N2 详情 详情
(V) 64329 1-(4-{[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy}phenyl)piperazine; [(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methyl 4-(1-piperazinyl)phenyl ether C24H27F2N5O2 详情 详情
(VI) 64326 2-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]-4-(4-bromophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one C20H22BrN3O2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(III)

Alternatively, the condensation of with the 4-bromophenyltriazolone (VI) with piperazine (IV) by means of Pd2(dba)3, BINAP and t-BuONa in hot toluene gives the monosubstituted piperazine (VII), which is then condensed with the already reported aryl ether (III) by means of Pd2(dba)3, BINAP and t-BuONa in hot toluene, and debenzylated with Pd/C and formic acid to afford the target disubstituted piperazine.

1 Hepperle, M.; Eckert, J.; Gala, D.; Shen, L.; Evans, C.A.; Goodman, A.; Mono N-arylation of piperazine(III): Metal-catalyzed N-arylation and its application to the novel preparations of the antifungal posaconazole and its advanced intermediate. Tetrahedron Lett 2002, 43, 18, 3359.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(III) 64328 1-{[(2R,4R)-4-[(4-bromophenoxy)methyl]-2-(2,4-difluorophenyl)tetrahydro-2-furanyl]methyl}-1H-1,2,4-triazole; 4-bromophenyl [(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methyl ether C20H18BrF2N3O2 详情 详情
(IV) 10355 Diethylenediamine; Piperazine 110-85-0 C4H10N2 详情 详情
(VI) 64326 2-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]-4-(4-bromophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one C20H22BrN3O2 详情 详情
(VII) 64327 2-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]-4-[4-(1-piperazinyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one C24H31N5O2 详情 详情
Extended Information