4-(4-chlorobutyl)pyridine -Drug Synthesis Database

【结构式】

【分子编号】59551

【品名】4-(4-chlorobutyl)pyridine

【CA登记号】

【分子式】C₉H₁₂ClN

【分子量】169.65372

【元素组成】C 63.72% H 7.13% Cl 20.9% N 8.26%

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：(XXII)

In a different strategy, the lithium derivative of 4-picoline (XVII) was alkylated with 2-(3-bromopropoxy)tetrahydropyran (XVIII) to afford (XIX). Acidic hydrolysis of the tetrahydropyranyl protecting group furnished 4-(4-pyridinyl)butanol (XX). Alternatively, lithiation of 4-picoline (XVII), followed by alkylation with 1-bromo-3-chloropropane (XXI) gave rise to 4-(4-pyridinyl)butyl chloride (XXII).

参考文献中间体

合成目标

【1】 Chung, J.Y.L.; Zhao, D.; Hughes, D.L. (Merck & Co., Inc.); Process for preparing fibrinogen receptor antagonists. US 5312923; WO 9316994 .
【2】 Chung, J.Y.L.; Zhao, D.; Hughes, D.L. (Merck & Co., Inc.); Process for preparing fibrinogen receptor antagonists. WO 9316995 .
【3】 Chung, J.Y.L.; Zhao, D.; Hughes, D.L.; Grabowski, E.E.; A practical synthesis of fibrinogen receptor antagonist MK-383 - Selective functionalization of (S)-tyrosine. Tetrahedron 1993, 49, 26, 5767.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XVII)	31150	4-methylpyridine	108-89-4	C₆H₇N	详情	详情
(XVIII)	42252	3-bromopropyl tetrahydro-2H-pyran-2-yl ether; 2-(3-bromopropoxy)tetrahydro-2H-pyran		C₈H₁₅BrO₂	详情	详情
(XIX)	59549	4-(4-pyridinyl)butyl tetrahydro-2H-pyran-2-yl ether; 4-[4-(tetrahydro-2H-pyran-2-yloxy)butyl]pyridine		C₁₄H₂₁NO₂	详情	详情
(XX)	59550	4-(4-pyridinyl)-1-butanol		C₉H₁₃NO	详情	详情
(XXI)	10358	1-Bromo-3-chloropropane	109-70-6	C₃H₆BrCl	详情	详情
(XXII)	59551	4-(4-chlorobutyl)pyridine		C₉H₁₂ClN	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XXII)

In a variation of this process, L-tyrosine (XXVII) was initially protected as the bis-O-silylated derivative (XXVIII) employing N,O-bis(trimethylsilyl) trifluoroacetamide. Acylation of (XXVIII) with butanesulfonyl chloride (XIV), followed by hydrolysis of the silyl groups, gave rise to N-butanesulfonyl tyrosine (XXIX). The phenolic hydroxyl of (XXIX) was then alkylated by 4-(4-pyridinyl)butyl chloride (XXII) to produce ether (XXVI). Finally, hydrogenation of the pyridine ring furnished the target piperidine derivative, which was isolated as the corresponding hydrochloride salt.

参考文献中间体

合成目标

【1】 Chung, J.Y.L.; Zhao, D.; Hughes, D.L. (Merck & Co., Inc.); Process for preparing fibrinogen receptor antagonists. WO 9316995 .
【2】 Chung, J.Y.L.; Zhao, D.; Hughes, D.L.; Grabowski, E.E.; A practical synthesis of fibrinogen receptor antagonist MK-383 - Selective functionalization of (S)-tyrosine. Tetrahedron 1993, 49, 26, 5767.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIV)	26779	1-butanesulfonyl chloride	2386-60-9	C₄H₉ClO₂S	详情	详情
(XXII)	59551	4-(4-chlorobutyl)pyridine		C₉H₁₂ClN	详情	详情
(XXVI)	59554	(2S)-2-[(butylsulfonyl)amino]-3-{4-[4-(4-pyridinyl)butoxy]phenyl}propanoic acid		C₂₂H₃₀N₂O₅S	详情	详情
(XXVII)	48794	(S)-(-)-Tyrosine; (S)-2-Amino-3-(4-hydroxyphenyl)propionic acid; 3-(4-Hydroxyphenyl)-L-alanine; L-(-)-Tyrosine; L-3-(4-Hydroxyphenyl)alanine; L-4-Hydroxy-17O-phenylalanine; L-beta-(p-Hydroxyphenyl)alanine; L-Hydroxy Phenyl Alanine; L-tyrosine	60-18-4	C₉H₁₁NO₃	详情	详情
(XXVIII)	59555	trimethylsilyl (2S)-2-amino-3-{4-[(trimethylsilyl)oxy]phenyl}propanoate		C₁₅H₂₇NO₃Si₂	详情	详情
(XXIX)	59556	(2S)-2-[(butylsulfonyl)amino]-3-(4-hydroxyphenyl)propanoic acid		C₁₃H₁₉NO₅S	详情	详情

Extended Information