2-thienylmethylamine; 2-thienylmethanamine -Drug Synthesis Database

【结构式】

【分子编号】33238

【品名】2-thienylmethylamine; 2-thienylmethanamine

【CA登记号】27757-85-3

【分子式】C₅H₇NS

【分子量】113.18332

【元素组成】C 53.06% H 6.23% N 12.38% S 28.33%

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 2-fluoro-4-chloro-5-sulfamoylbenzoic acid (I) with refluxing SOCl2 gives the corresponding acyl chloride (II), which by reaction with aqueous NH3 is transformed into the amide (III). The dehydration of (III) with refluxing POCl3 affords the nitrile (IV), which is then condensed with thenylamine (V) to yield 4-chloro-2-thenylamino-5-sulfamoylbenzonitrile (VI). Finally, this compound is cyclized with sodium azide in DMF at 100 C.

参考文献中间体

合成目标

【1】 Popelak, A.; et al. (Boehringer Ingelheim GmbH); 5-Phenyltetrazole derivatives. DE 1815922; FR 2026688; GB 1237790; US 3665002 .
【2】 Serradell, M.N.; Castaner, J.; Blancafort, P.; Hillier, K.; Azosemide. Drugs Fut 1979, 4, 6, 393.

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)	33234	5-(aminosulfonyl)-4-chloro-2-fluorobenzoic acid		C₇H₅ClFNO₄S	详情	详情
(II)	33235	5-(aminosulfonyl)-4-chloro-2-fluorobenzoyl chloride		C₇H₄Cl₂FNO₃S	详情	详情
(III)	33236	5-(aminosulfonyl)-4-chloro-2-fluorobenzamide		C₇H₆ClFN₂O₃S	详情	详情
(IV)	33237	2-chloro-5-cyano-4-fluorobenzenesulfonamide		C₇H₄ClFN₂O₂S	详情	详情
(V)	33238	2-thienylmethylamine; 2-thienylmethanamine	27757-85-3	C₅H₇NS	详情	详情
(VI)	33239	2-chloro-5-cyano-4-[(2-thienylmethyl)amino]benzenesulfonamide		C₁₂H₁₀ClN₃O₂S₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Reductive condensation of 2-thienylmethylamine (I) with 2-thiophenecarboxaldehyde (II) in the presence of NaBH(OAc)3 provided bis(2-thienylmethyl)amine (III), which was coupled with N-Boc-2-aminohexanoic acid (IV) by means of EDC and HOBt, yielding amide (V). Acid deprotection of the Boc group of (V) then gave amine (VI).

参考文献中间体

合成目标

【1】 Scott, I.L.; et al.; Novel N,N-disubstituted amides that are highly potent VLA-4 antagonists. 219th ACS Natl Meet (March 26 2000, San Francisco) 2000, Abst MEDI 284.
【2】 Raju, B.G.; Scott, I.L.; Biediger, R.J.; Market, R.V.; Grabbe, V.O.; Kassir, J.M.; Kogan, T.P.; Lin, S. (Texas Biotechnology Corp.); N,N-Disubstd. amides that inhibit the binding of integrins to their receptors. US 6096773; WO 9952493; WO 9952898 .

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)	33238	2-thienylmethylamine; 2-thienylmethanamine	27757-85-3	C₅H₇NS	详情	详情
(II)	30732	2-thiophenecarbaldehyde; Thiophene-2-carboxaldehyde	98-03-3	C₅H₄OS	详情	详情
(III)	38466	2-thienyl-N-(2-thienylmethyl)methanamine; N,N-bis(2-thienylmethyl)amine		C₁₀H₁₁NS₂	详情	详情
(IV)	20398	(2S)-2-[(tert-butoxycarbonyl)amino]hexanoic acid		C₁₁H₂₁NO₄	详情	详情
(V)	38467	tert-butyl (1S)-1-[[bis(2-thienylmethyl)amino]carbonyl]pentylcarbamate		C₂₁H₃₀N₂O₃S₂	详情	详情
(VI)	38468	(2S)-2-amino-N,N-bis(2-thienylmethyl)hexanamide		C₁₆H₂₂N₂OS₂	详情	详情

Extended Information