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【结 构 式】

【分子编号】27114

【品名】phenyl(1-[2-[4-(4-piperidinyloxy)-2-(2,2,2-trifluoroethoxy)phenyl]acetyl]-4-piperidinyl)formamide

【CA登记号】

【 分 子 式 】C27H32F3N3O4

【 分 子 量 】519.5641096

【元素组成】C 62.42% H 6.21% F 10.97% N 8.09% O 12.32%

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:(XIV)

Regioselective Mitsunobu condensation of 2',4'-dihydroxyacetophenone (VII) with N-Boc-4-piperidinol (VIII) afforded ether (IX). The 2'-hydroxyl group of (IX) was then alkylated with 2,2,2-trifluoroethyl trifluoromethanesulfonate in the presence of Cs2CO3 to give (X). Oxidative rearrangement of the acetophenone (X) employing thallium trinitrate and trimethyl orthoformate generated the phenylacetic ester (XI), which was hydrolyzed to acid (XII) with NaOH in aqueous MeOH. Subsequent EDC-mediated coupling of (XII) with piperidine intermediate (VI) yielded amide (XIII). The N-Boc group of (XIII) was cleaved using HCl in EtOAc, and the secondary amine (XIV) was acylated with acetic anhydride in the presence of diisopropyl ethylamine to afford the target acetamide.

1 Bock, M.G.; Evans, B.E.; Williams, P.D.; et al.; Nonpeptide oxytocin antagonists: Analogs of L-371,257 with improved potency. Bioorg Med Chem Lett 1999, 9, 9, 1311.
2 Freidinger, R.M.; Stauffer, K.; Perlow, D.S.; Sparks, M.A.; Williams, P.D.; Bell, I.M. (Merck & Co., Inc.); Tocolytic oxytocin receptor antagonists. GB 2326410; US 6090805 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
40675 2,2,2-trifluoroethyl trifluoromethanesulfonate 6226-25-1 C3H2F6O3S 详情 详情
(VI) 19420 1-(4-piperidinyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one C13H16N2O2 详情 详情
(VII) 13961 Resacetophenone; 1-(2,4-Dihydroxyphenyl)-1-ethanone 89-84-9 C8H8O3 详情 详情
(VIII) 18625 tert-butyl 4-hydroxy-1-piperidinecarboxylate C10H19NO3 详情 详情
(X) 27110 tert-butyl 4-[4-acetyl-3-(2,2,2-trifluoroethoxy)phenoxy]-1-piperidinecarboxylate C20H26F3NO5 详情 详情
(XI) 27111 tert-butyl 4-[4-(2-methoxy-2-oxoethyl)-3-(2,2,2-trifluoroethoxy)phenoxy]-1-piperidinecarboxylate C21H28F3NO6 详情 详情
(XII) 27112 2-[4-[[1-(tert-butoxycarbonyl)-4-piperidinyl]oxy]-2-(2,2,2-trifluoroethoxy)phenyl]acetic acid C20H26F3NO6 详情 详情
(XIII) 27113 tert-butyl 4-[4-(2-oxo-2-[4-[2-oxo-2H-3,1-benzoxazin-1(4H)-yl]-1-piperidinyl]ethyl)-3-(2,2,2-trifluoroethoxy)phenoxy]-1-piperidinecarboxylate C33H40F3N3O7 详情 详情
(XIV) 27114 phenyl(1-[2-[4-(4-piperidinyloxy)-2-(2,2,2-trifluoroethoxy)phenyl]acetyl]-4-piperidinyl)formamide C27H32F3N3O4 详情 详情
Extended Information