[[amino(imino)methyl]sulfanyl]methane -Drug Synthesis Database

【结构式】

【分子编号】44636

【品名】[[amino(imino)methyl]sulfanyl]methane

【CA登记号】

【分子式】C₂H₆N₂S

【分子量】90.14912

【元素组成】C 26.65% H 6.71% N 31.07% S 35.57%

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：(I)

The synthesis of [14C]-labeled 15-deoxyspergualin trihydrochloride has been reported: The condensation of [14C]-labeled S-methylisothiourea (I) with 7-aminoheptanoic acid (II) by means of NaOH in water gives 7-guanidinoheptanoic acid (III), which is treated with Dowex 50W resin (H+ form) in refluxing methanol yielding the corresponding methyl ester (IV). The reaction of (IV) with concentrated NH4OH affords the amide (V), which is finally condensed with glyoxyloxyspermidine (VI) by means of glutaric acid in hot water (60 C), and purified by chromatography over Sephadex CM-25 (Na+ form).

参考文献中间体

合成目标

【1】 Dischino, D.D.; Synthesis of carbon-14 labeled (±) 15-deoxyspergualin trihydrochloride. J Label Compd Radiopharm 1995, 36, 11, 1097.

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)	10272	[[Amino(imino)methyl]sulfanyl]methane	2986-19-8	C₂H₆N₂S	详情	详情
(I)	44636	[[amino(imino)methyl]sulfanyl]methane		C₂H₆N₂S	详情	详情
(II)	10273	7-Aminoheptanoic acid	929-17-9	C₇H₁₅NO₂	详情	详情
(III)	10274	7-[[Amino(imino)methyl]amino]heptanoic acid		C₈H₁₇N₃O₂	详情	详情
(III)	44637	7-[[amino(imino)methyl]amino]heptanoic acid		C₈H₁₇N₃O₂	详情	详情
(IV)	10275	methyl 7-[[amino(imino)methyl]amino]heptanoate		C₉H₁₉N₃O₂	详情	详情
(IV)	44638	methyl 7-[[amino(imino)methyl]amino]heptanoate		C₉H₁₉N₃O₂	详情	详情
(V)	10270	7-[[Amino(imino)methyl]amino]heptanamide		C₈H₁₈N₄O	详情	详情
(V)	44639	7-[[amino(imino)methyl]amino]heptanamide		C₈H₁₈N₄O	详情	详情
(VI)	10271	N-[4-[(3-Aminopropyl)amino]butyl]-2,2-dihydroxyacetamide		C₉H₂₁N₃O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

An improved synthesis of [14C]-peldesine has been reported: The reaction of S-methyl-[14C]-isothiourea (I) with methyl chloroformate (II) by means of tetrabutylammonium bromide in dichloromethane gives N,N'-bis(methoxycarbonyl)-S-methyl-[14C]-isothiourea (III). This compound is condensed with 3-amino-4-(3-pyridylmethyl)-1H-pyrrole-2-carboxylic acid methyl ester (IV) by means of acetic acid in methanol yielding the labeled guanidine (V). The cyclization of (V) by means of sodium methoxide in methanol affords the carbamate precursor (VI), which is finally deprotected with NaOH in hot water.

参考文献中间体

合成目标

【1】 Elliott, A.J.; Kwong, C.D.; Montgomery, J.A.; An improved synthesis of 9-(3-pyridylmethyl)-[2-14C]-9-deazaguanine. J Label Compd Radiopharm 1998, 41, 10, 879.

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)	10272	[[Amino(imino)methyl]sulfanyl]methane	2986-19-8	C₂H₆N₂S	详情	详情
(I)	44636	[[amino(imino)methyl]sulfanyl]methane		C₂H₆N₂S	详情	详情
(II)	16993	methyl chlorocarbonate;Carbonochloridic acid methyl ester；[(chlorocarbonyl)oxy]methane；methyl chloroformate	79-22-1	C₂H₃ClO₂	详情	详情
(III)	28696	methyl (Z)-[(methoxycarbonyl)amino](methylsulfanyl)methylidenecarbamate		C₆H₁₀N₂O₄S	详情	详情
(III)	45292	methyl (Z)-[(methoxycarbonyl)amino](methylsulfanyl)methylidenecarbamate		C₆H₁₀N₂O₄S	详情	详情
(IV)	16030	methyl 3-amino-4-(3-pyridinylmethyl)-1H-pyrrole-2-carboxylate		C₁₂H₁₃N₃O₂	详情	详情
(V)	28697	methyl 3-([bis[(methoxycarbonyl)amino]methylene]amino)-4-(3-pyridinylmethyl)-1H-pyrrole-2-carboxylate		C₁₇H₁₉N₅O₆	详情	详情
(V)	45293	methyl 3-([bis[(methoxycarbonyl)amino]methylene]amino)-4-(3-pyridinylmethyl)-1H-pyrrole-2-carboxylate		C₁₇H₁₉N₅O₆	详情	详情
(VI)	28698	methyl 4-oxo-7-(3-pyridinylmethyl)-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-ylcarbamate		C₁₄H₁₃N₅O₃	详情	详情
(VI)	45294	methyl 4-oxo-7-(3-pyridinylmethyl)-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-ylcarbamate		C₁₄H₁₃N₅O₃	详情	详情

Extended Information