2-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]-4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one -Drug Synthesis Database

【结构式】

【分子编号】21196

【品名】2-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]-4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

【CA登记号】

【分子式】C₄₄H₄₈F₂N₈O₄

【分子量】790.9134464

【元素组成】C 66.82% H 6.12% F 4.8% N 14.17% O 8.09%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

The synthesis of [14C]-SCH-56592 has been described: The cyclization of semicarbazide (I) with [14C]-formamidine (II) in hot 2-methoxyethanol gives the triazolone (III), which is condensed with the sulfonate (IV) by means of Cs2CO3 in hot DMF to yield the alkylated triazolone (V). Finally, this compound is deprotected by hydrogenation with formic acid over Pd/C in hot methanol to afford labeled SCH-56592.

参考文献中间体

合成目标

【1】 Magatti, C.V.; et al.; Synthesis of H-3-SCH 51048 and C-14-SCH 56592. J Label Compd Radiopharm 1998, 41, 8, 731.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	21192	N-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-1-hydrazinecarboxamide	C₃₁H₃₄F₂N₈O₃	详情	详情
(II)	21193	iminoformamide	CH₄N₂	详情	详情
(III)	16351	4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one	C₃₂H₃₂F₂N₈O₃	详情	详情
(III)	21194	4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one	C₃₂H₃₂F₂N₈O₃	详情	详情
(IV)	21195	(1R,2S)-2-(benzyloxy)-1-ethylpropyl 4-bromobenzenesulfonate	C₁₈H₂₁BrO₄S	详情	详情
(V)	21196	2-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]-4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one	C₄₄H₄₈F₂N₈O₄	详情	详情
(V)	34853	2-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]-4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one	C₄₄H₄₈F₂N₈O₄	详情	详情
(VI)	21197	4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-2-[(1S,2S)-1-ethyl-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one	C₃₇H₄₂F₂N₈O₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

参考文献中间体

合成目标

【1】 Saksena AK, Girijavallabhan VM, Lovey RG, et al. 1995. Tetrahydrofuran antifungals. W0 9517407
【2】 Saksena AK, Girijavallabhan VM, Wang HY, et aL. 2004. Stereoselective grignard additions to N-formyl hydrazone: a concise synthesis of NoxafilR side chain and a synthesis of NonfilR. Tetrahedron Lett, 45: 8249～8251

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)	17100	(2S)-2-(benzyloxy)-1-(1-pyrrolidinyl)-1-propanone	122151-32-0	C₁₄H₁₉NO₂	详情	详情
(II)	66599	(S)-2-(benzyloxy)propanal	81445-44-5	C₁₀H₁₂O₂	详情	详情
(III)	66600	(S,E)-N'-(2-(benzyloxy)propylidene)formohydrazide		C₁₁H₁₄N₂O₂	详情	详情
(IV)	17106	N'-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]formic hydrazide		C₁₃H₂₀N₂O₂	详情	详情
(V)	17071	N-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-N-(1-phenoxyvinyl)amine		C₃₈H₃₈F₂N₆O₃	详情	详情
(VI)	21196	2-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]-4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one		C₄₄H₄₈F₂N₈O₄	详情	详情

Extended Information