2-(Methylsulfanyl)ethylamine; 2-(Methylthio)ethylamine; 2-(Methylsulfanyl)-1-ethanamine -Drug Synthesis Database

【结构式】

【分子编号】11240

【品名】2-(Methylsulfanyl)ethylamine; 2-(Methylthio)ethylamine; 2-(Methylsulfanyl)-1-ethanamine

【CA登记号】18542-42-2

【分子式】C₃H₉NS

【分子量】91.1772

【元素组成】C 39.52% H 9.95% N 15.36% S 35.17%

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 reaction of 4-nitrophenol (I) with 2-chloroethyl isocyanate (II) in pyridine leads to the activated carbamate (III), which is nitrosated by reacting with nitrosyl chloride in pyridine at -20 C to yield 4-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate (IV). The nitrosated molecule (IV) is reacted with 2-(methylthio)ethylamine (V) in THF at ordinary temperature affording the sulfure urea (VI), which is then oxidized to the sulfonyl compound (VII) by hydrogen peroxide in formic acid at 50 C.

参考文献中间体

合成目标

【1】 Godeneche, D.; Imbach, J.-L.; Madelmont, J.-C.; Meyniel, G.; Moreau, M.-F.; Oiry, J.; Parry, D. (CNRS (Centre National de la Recherche Scientifique); INSERM (Institut National de la Sante et de la Recherche Medicale)); Novel nitrosourea cpds. Process of preparation. Compsns. based on these cpds. useful in anticancer chemotherapy. EP 0185020; FR 2562890; JP 1988502269; WO 8504655 .
【2】 Madelmont, J.-C.; Godeneche, D.; Moreau, M.-F.; Parry, D.; Meyniel, G.; Oiry, J.; Imbach, J.-L. (CNRS (Centre National de la Recherche Scientifique); INSERM (Institut National de la Sante et de la Recherche Medicale)); Nitrosoureas compounds, preparation thereof and utilization thereof in anticancerous. US 5001158 .
【3】 Meyniel, G.; Duprat, J.; Mathe, G.; Plagne, R.; Godeneche, D.; Parry, D.; Madelmont, J.C.; Chabard, J.L.; New cysteamin(2-chloroethyl)nitrosoureas. Synthesis and preliminary antitumor results. J Med Chem 1985, 28, 9, 1346-50.
【4】 Madelmont, J.C.; Cystemustine. Drugs Fut 1994, 19, 1, 27.

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)	11236	4-Nitrophenol; p-Nitrophenol	100-02-7	C₆H₅NO₃	详情	详情
(II)	11237	1-Chloro-2-isocyanatoethane; 2-Chloroethyl isocyanate	1943-83-5	C₃H₄ClNO	详情	详情
(III)	11238	4-nitrophenyl N-(2-chloroethyl)carbamate		C₉H₉ClN₂O₄	详情	详情
(IV)	11239	4-nitrophenyl 1-(2-chloroethyl)-2-oxo-1-hydrazinecarboxylate		C₉H₈ClN₃O₅	详情	详情
(V)	11240	2-(Methylsulfanyl)ethylamine; 2-(Methylthio)ethylamine; 2-(Methylsulfanyl)-1-ethanamine	18542-42-2	C₃H₉NS	详情	详情
(VI)	11241	1-(2-Chloroethyl)-N-[2-(methylsulfanyl)ethyl]-2-oxo-1-hydrazinecarboxamide		C₆H₁₂ClN₃O₂S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

参考文献中间体

合成目标

【1】 Petrov KG, Zhang YM, Carter M, et al. 2006. Optimization and SAR for dual ErbB-1/ErbB-2 tyrosine kinase inhibition in the 6-furanylquinazoline series. Bioorganic & Medicinal Chemistry Letters, 16, 4686～4691.

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)	11240	2-(Methylsulfanyl)ethylamine; 2-(Methylthio)ethylamine; 2-(Methylsulfanyl)-1-ethanamine	18542-42-2	C₃H₉NS	详情	详情
(II)	67211	benzyl (2-(methylthio)ethyl)carbamate		C₁₁H₁₅NO₂S	详情	详情
(III)	67212	benzyl (2-(methylsulfonyl)ethyl)carbamate		C₁₁H₁₅NO₄S	详情	详情
(IV)	49880	2-(methylsulfonyl)-1-ethanamine; 2-(methylsulfonyl)ethylamine		C₃H₉NO₂S	详情	详情
(VI)	49872	1-Chloro-2-Hydroxy-5-Nitrobenzene; 2-Chloro-4-nitrophenol; 4-Nitro-2-chlorophenol; p-Nitro-o-chlorophenol	619-08-9	C₆H₄ClNO₃	详情	详情
(VII)	17221	3-Fluorobenzyl bromide; 1-(bromomethyl)-3-fluorobenzene	456-41-7	C₇H₆BrF	详情	详情
(VIII)	49873	2-chloro-1-[(3-fluorobenzyl)oxy]-4-nitrobenzene; 2-chloro-4-nitrophenyl 3-fluorobenzyl ether		C₁₃H₉ClFNO₃	详情	详情
(IX)	49874	3-chloro-4-[(3-fluorobenzyl)oxy]phenylamine; 3-chloro-4-[(3-fluorobenzyl)oxy]aniline		C₁₃H₁₁ClFNO	详情	详情
(X)	49875	4-chloro-6-iodoquinazoline	98556-31-1	C₈H₄ClIN₂	详情	详情
(XI)	49876	N-[3-chloro-4-[(3-fluorobenzyl)oxy]phenyl]-N-(6-iodo-4-quinazolinyl)amine; N-[3-chloro-4-[(3-fluorobenzyl)oxy]phenyl]-6-iodo-4-quinazolinamine		C₂₁H₁₄ClFIN₃O	详情	详情
(XII)	67214	(5-formylfuran-2-yl)boronic acid	27329-70-0	C₅H₅BO₄	详情	详情
(XIII)	49879	5-(4-[3-chloro-4-[(3-fluorobenzyl)oxy]anilino]-6-quinazolinyl)-2-furaldehyde		C₂₆H₁₇ClFN₃O₃	详情	详情

Extended Information