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【结 构 式】

【分子编号】44195

【品名】5-(hydroxymethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

【CA登记号】

【 分 子 式 】C3H5N3O2

【 分 子 量 】115.09172

【元素组成】C 31.31% H 4.38% N 36.51% O 27.8%

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:(XXXII)

Synthesis of 250157: Alternatively, the final compound can be obtained by direct condensation of (VI) with chlorotriazolinone (XXVI) in DMF/H2O in the presence of K2CO3 or DIEA. For the obtention of (XXVI), two routes can be followed: 1. Reaction of semicarbazide (XXVII) with orthoester (XXVIII) in MeOH; and 2. Condensation of semicarbazide (XXVII) with benzyloxyacetyl chloride (XXIX) in THF/H2O in the presence of NaOH to provide adduct (XXX), which is then cyclized by means of refluxing NaOH to afford triazolinone (XXXI). Debenzylation of (XXXI) by hydrogenation over Pd/C in MeOH/H2O yields alcohol (XXXII), which is finally treated with thionyl chloride.

1 Castaner, J.; Silvestre, J.S.; Bayes, M.; Sorbera, L.A.; Aprepitant and L-758298. Drugs Fut 2002, 27, 3, 211.
2 Cowden, C.J.; et al.; A new synthesis of 1,2,4-triazolin-5-ones: Application to the convergent synthesis of an NK1 antagonist. Tetrahedron Lett 2000, 41, 44, 8661.
3 Cowden, C.J. (Merck Sharp & Dohme Ltd.); Process for the preparation of 1,2,4-triazolin-5-one derivs.. WO 0196315 .
4 Dolling, U.H.; Wilson, R.D.; Hands, D.; Cottrell, I.F. (Merck Sharp & Dohme Ltd.); Chemical synthesis of morpholine derivs.. WO 9965900 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VI) 18293 (1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl (2R,3S)-3-(4-fluorophenyl)morpholinyl ether; (2R,3S)-2-([(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]oxy)-3-(4-fluorophenyl)morpholine 171482-05-6 C20H18F7NO2 详情 详情
(XXVI) 44196 5-(chloromethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one C3H4ClN3O 详情 详情
(XXVII) 23944 1-Hydrazinecarboxamide 563-41-7 CH5N3O 详情 详情
(XXVIII) 44197 2-chloro-1,1-dimethoxyethyl methyl ether; 2-chloro-1,1,1-trimethoxyethane C5H11ClO3 详情 详情
(XXIX) 10493 2-(Benzyloxy)acetyl chloride; Benzyloxyacetyl chloride 19810-31-2 C9H9ClO2 详情 详情
(XXX) 44193 2-[2-(benzyloxy)acetyl]-1-hydrazinecarboxamide C10H13N3O3 详情 详情
(XXXI) 44194 5-[(benzyloxy)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one C10H11N3O2 详情 详情
(XXXII) 44195 5-(hydroxymethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one C3H5N3O2 详情 详情
Extended Information