3-(benzyloxy)-1-methyl-4-[(2-thioxo-1,3-thiazolidin-3-yl)carbonyl]-2(1H)-pyridinone -Drug Synthesis Database

【结构式】

【分子编号】48345

【品名】3-(benzyloxy)-1-methyl-4-[(2-thioxo-1,3-thiazolidin-3-yl)carbonyl]-2(1H)-pyridinone

【CA登记号】

【分子式】C₁₇H₁₆N₂O₃S₂

【分子量】360.45772

【元素组成】C 56.65% H 4.47% N 7.77% O 13.32% S 17.79%

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：(IV)

The reductive condensation of ammonium acetate with three molecules of N-Boc-O-benzyl-L-serinal (I) in the presence of sodium triacetoxyborohydride produced the tertiary amine (II). Subsequent removal of the Boc protecting groups of (II) by means of trifluoroacetic acid gave the tetra-amine (III). This was coupled with the (pyridylcarbonyl)thiazolidinethione (IV) to furnish the tris-pyridinecarboxamide (V). Cleavage of the benzyl ether groups of (V) was achieved by treatment of (V) with HBr in AcOH to yield (VI). This was finally complexed with Gd+3 ion to form the title gadolinium chelate.

参考文献中间体

合成目标

【1】 Hajela, S.; et al.; A tris-hydroxymethyl-substituted derivative of Gd-TREN-Me-3,2-HOPO: An MRI relaxation agent with improved efficiency. J Am Chem Soc 2000, 122, 45, 11228.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	48342	tert-butyl (1S)-2-(benzyloxy)-1-formylethylcarbamate	C₁₅H₂₁NO₄	详情	详情
(II)	48343	tert-butyl (1R)-2-(benzyloxy)-1-[(bis[(2R)-3-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]propyl]amino)methyl]ethylcarbamate	C₄₅H₆₆N₄O₉	详情	详情
(III)	48344	N,N,N-tris[(2R)-2-amino-3-(benzyloxy)propyl]amine; (2R)-N(1),N(1)-bis[(2R)-2-amino-3-(benzyloxy)propyl]-3-(benzyloxy)-1,2-propanediamine	C₃₀H₄₂N₄O₃	详情	详情
(IV)	48345	3-(benzyloxy)-1-methyl-4-[(2-thioxo-1,3-thiazolidin-3-yl)carbonyl]-2(1H)-pyridinone	C₁₇H₁₆N₂O₃S₂	详情	详情
(V)	48346	3-(benzyloxy)-N-[(1R)-2-(benzyloxy)-1-([bis[(2R)-3-(benzyloxy)-2-([[3-(benzyloxy)-1-methyl-2-oxo-1,2-dihydro-4-pyridinyl]carbonyl]amino)propyl]amino]methyl)ethyl]-1-methyl-2-oxo-1,2-dihydro-4-pyridinecarboxamide	C₇₂H₇₅N₇O₁₂	详情	详情
(VI)	48347	N-[(1R)-2-[bis((2R)-3-hydroxy-2-[[(3-hydroxy-1-methyl-2-oxo-1,2-dihydro-4-pyridinyl)carbonyl]amino]propyl)amino]-1-(hydroxymethyl)ethyl]-3-hydroxy-1-methyl-2-oxo-1,2-dihydro-4-pyridinecarboxamide	C₃₀H₃₉N₇O₁₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

Acylation of the primary amino groups of spermine (V) by the N acyl thiazolide (VI) furnishes diamide (VII). This is further coupled with acid chloride (IV) producing tetraamide (VIII). Finally, deprotection of the O-benzyl groups under acidic conditions gives rise to the title compound.

参考文献中间体

合成目标

【1】 Xu, J.; et al.; Synthesis and initial evaluation for in vivo chelation of Pu(IV) of a mixed octadentate spermine-based ligand containing 4-carbamoyl-3-hydroxy-1-methyl-2(1H)-pyridinone and 6-carbamoyl-1-hydroxy-2(1H)-pyridinone. J Med Chem 2002, 45, 18, 3963.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(IV)	61993	1-(benzyloxy)-6-oxo-1,6-dihydro-2-pyridinecarbonyl chloride	C₁₃H₁₀ClNO₃	详情	详情
(V)	46326	N-(3-aminopropyl)-N-[4-[(3-aminopropyl)amino]butyl]amine; N(1),N(4)-bis(3-aminopropyl)-1,4-butanediamine	C₁₀H₂₆N₄	详情	详情
(VI)	48345	3-(benzyloxy)-1-methyl-4-[(2-thioxo-1,3-thiazolidin-3-yl)carbonyl]-2(1H)-pyridinone	C₁₇H₁₆N₂O₃S₂	详情	详情
(VII)	61994	3-(benzyloxy)-N-{3-[(4-{[3-({[3-(benzyloxy)-1-methyl-2-oxo-1,2-dihydro-4-pyridinyl]carbonyl}amino)propyl]amino}butyl)amino]propyl}-1-methyl-2-oxo-1,2-dihydro-4-pyridinecarboxamide	C₃₈H₄₈N₆O₆	详情	详情
(VIII)	61995	1-(benzyloxy)-N-[3-({[3-(benzyloxy)-1-methyl-2-oxo-1,2-dihydro-4-pyridinyl]carbonyl}amino)propyl]-N-[4-([3-({[3-(benzyloxy)-1-methyl-2-oxo-1,2-dihydro-4-pyridinyl]carbonyl}amino)propyl]{[1-(benzyloxy)-6-oxo-1,6-dihydro-2-pyridinyl]carbonyl}amino)but	C₆₄H₆₆N₈O₁₂	详情	详情

Extended Information