methyl 2-thiophenecarbimidothioate -Drug Synthesis Database

【结构式】

【分子编号】34836

【品名】methyl 2-thiophenecarbimidothioate

【CA登记号】

【分子式】C₆H₇NS₂

【分子量】157.26032

【元素组成】C 45.83% H 4.49% N 8.91% S 40.78%

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)

(S)-6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (I) was coupled to N-(4-nitrophenyl)piperazine (II) via activation with 1,1'-carbonyldiimidazole to furnish the corresponding amide (III). Subsequent hydrogenation of the nitro group of (III) over Pd/C provided aniline (IV). This was finally condensed with S-methyl-2-thiophenethiocarboxamide (V) to yield the title amidine.

参考文献中间体

合成目标

【1】 Chabrier de Lassauniere, P.-E.; Auguet, M.; Auvin, S.; Bigg, D. (SCRAS (Societé de Conseils de Recherches et d'Applications Scientifiques)); Novel 2-(iminomethyl)amino-phenyl derivs., preparation, application as medicines and pharmaceutical compsns. containing same. EP 0973763; WO 9842696 .

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)	34833	(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carboxylic acid		C₁₄H₁₈O₄	详情	详情
(II)	20299	1-(4-nitrophenyl)piperazine	6269-89-2	C₁₀H₁₃N₃O₂	详情	详情
(III)	34834	[(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl][4-(4-nitrophenyl)-1-piperazinyl]methanone		C₂₄H₂₉N₃O₅	详情	详情
(IV)	34835	[4-(4-aminophenyl)-1-piperazinyl][(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methanone		C₂₄H₃₁N₃O₃	详情	详情
(V)	34836	methyl 2-thiophenecarbimidothioate		C₆H₇NS₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

Reduction of N-Boc-3-nitrobenzylamine (I) by catalytic hydrogenation over Pd/C yields aniline (II). This is then condensed with S-methyl-2-thiophenethiocarboximide (III) to furnish amidine (IV). Subsequent acidic Boc group cleavage yields amine (V).

参考文献中间体

合成目标

【1】 Auvin, S.; Auget, M.; Navet, E.; Harnett, J.J.; Viossat, I.; Schulz, J.; Bigg, D.; Chabrier, P.-E.; Novel inhibitors of neuronal nitric oxide synthase with potent antioxidant properties. Bioorg Med Chem Lett 2003, 13, 2, 209.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	63368	1,1-dimethylethyl (3-nitrophenyl)methylcarbamate	C₁₂H₁₆N₂O₄	详情	详情
(II)	39660	tert-butyl 3-aminobenzylcarbamate	C₁₂H₁₈N₂O₂	详情	详情
(III)	34836	methyl 2-thiophenecarbimidothioate	C₆H₇NS₂	详情	详情
(IV)	63369	1,1-dimethylethyl (3-{[imino(2-thiophenyl)methyl]amino}phenyl)methylcarbamate	C₁₇H₂₁N₃O₂S	详情	详情
(V)	63370	N-[3-(aminomethyl)phenyl]-2-thiophenecarboximidamide	C₁₂H₁₃N₃S	详情	详情

Extended Information