2-(methylsulfonyl)-1-ethanamine; 2-(methylsulfonyl)ethylamine -Drug Synthesis Database

【结构式】

【分子编号】49880

【品名】2-(methylsulfonyl)-1-ethanamine; 2-(methylsulfonyl)ethylamine

【CA登记号】

【分子式】C₃H₉NO₂S

【分子量】123.176

【元素组成】C 29.25% H 7.36% N 11.37% O 25.98% S 26.03%

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：(X)

Williamson's ether synthesis between 2-chloro-4-nitrophenol (I) and 3-fluorobenzyl bromide (II) afforded ether (III). The nitro group of (III) was then reduced to the aniline (IV) by means of catalytic hydrogenation over Pt/C. Condensation of aniline (IV) with 4-chloro-6-iodoquinazoline (V) furnished the diaryl amine (VI). Subsequent Stille coupling between iodide (VI) and 5-dioxolanyl-2-(tributylstannyl)furan (VII) gave rise to adduct (VIII), which was further subjected to acid hydrolysis of the cyclic ketal to yield aldehyde (IX). Finally, reductive amination of (IX) with 2-(methanesulfonyl)ethylamine (X) in the presence of sodium triacetoxyborohydride provided the title compound.

参考文献中间体

合成目标

【1】 Guntrip, S.B.; Lackey, K.E.; Cockerill, G.S.; Carter, M.C.; Smith, K.J. (Glaxo Group Ltd.); Bicyclic heteroaromatic cpds. as protein tyrosine kinase inhibitors. EP 1047694; WO 9935146 .

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)	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
(II)	17221	3-Fluorobenzyl bromide; 1-(bromomethyl)-3-fluorobenzene	456-41-7	C₇H₆BrF	详情	详情
(III)	49873	2-chloro-1-[(3-fluorobenzyl)oxy]-4-nitrobenzene; 2-chloro-4-nitrophenyl 3-fluorobenzyl ether		C₁₃H₉ClFNO₃	详情	详情
(IV)	49874	3-chloro-4-[(3-fluorobenzyl)oxy]phenylamine; 3-chloro-4-[(3-fluorobenzyl)oxy]aniline		C₁₃H₁₁ClFNO	详情	详情
(V)	49875	4-chloro-6-iodoquinazoline	98556-31-1	C₈H₄ClIN₂	详情	详情
(VI)	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
(VII)	49877	tributyl[5-(1,3-dioxolan-2-yl)-2-furyl]stannane		C₁₉H₃₄O₃Sn	详情	详情
(VIII)	49878	N-[3-chloro-4-[(3-fluorobenzyl)oxy]phenyl]-6-[5-(1,3-dioxolan-2-yl)-2-furyl]-4-quinazolinamine; N-[3-chloro-4-[(3-fluorobenzyl)oxy]phenyl]-N-[6-[5-(1,3-dioxolan-2-yl)-2-furyl]-4-quinazolinyl]amine		C₂₈H₂₁ClFN₃O₄	详情	详情
(IX)	49879	5-(4-[3-chloro-4-[(3-fluorobenzyl)oxy]anilino]-6-quinazolinyl)-2-furaldehyde		C₂₆H₁₇ClFN₃O₃	详情	详情
(X)	49880	2-(methylsulfonyl)-1-ethanamine; 2-(methylsulfonyl)ethylamine		C₃H₉NO₂S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

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