2-pyridinylmethanol；pyridin-2-ylmethanol；2-pyridylmethanol -Drug Synthesis Database

【结构式】

【分子编号】30208

【品名】2-pyridinylmethanol；pyridin-2-ylmethanol；2-pyridylmethanol

【CA登记号】586-98-1

【分子式】C₆H₇NO

【分子量】109.12772

【元素组成】C 66.04% H 6.47% N 12.84% O 14.66%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(IV)

This compound can be obtained in two different ways: 1) By reaction of 2-(p-isobutylphenyl)propionic acid sodium salt (I) with 2-pyridylmethyl chloride (II) in refluxing benzene. 2) By reaction of 2-(p-isobutylphenyl)propionyl chloride (III) with 2-pyridylmethanol (IV) by means of triethylamine in THF.

参考文献中间体

合成目标

【1】 Noda, K.; Nakagawa, A.; Ishikura, Y.; Tosu, S.; Ide, H. (Hisamitsu Pharmaceutical Co., Ltd.); Pyridylalkyl esters of 2-(p-isobutylphenyl)acetic acid and propionic acids and use. US 4150137 .
【2】 Castaner, J.; Blancafort, P.; Serradell, M.N.; Pineprofen. Drugs Fut 1982, 7, 6, 401.

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)	31961	sodium 2-(4-isobutylphenyl)propanoate		C₁₃H₁₇NaO₂	详情	详情
(II)	26187	2-(Chloromethyl)pyridine	4377-33-7	C₆H₆ClN	详情	详情
(III)	22117	2-(4-isobutylphenyl)propanoyl chloride		C₁₃H₁₇ClO	详情	详情
(IV)	30208	2-pyridinylmethanol；pyridin-2-ylmethanol；2-pyridylmethanol	586-98-1	C₆H₇NO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The acylation of 2-pyridylmethanol (I) with thioacetic acid (II) by means of Ph3P and DEAD in THF gives the corresponding thioacetate (III), which is condensed with 4-acetoxyazetidin-2-one (IV) by means of NaOH in methanol yielding 4-(2-pyridylmethylsulfanyl)azetidin-2-one (V). Finally, this compound is condensed with 1(R)-phenylethyl isocyanate (VI) by means of Et3N and DMAP in dichloromethane.

参考文献中间体

合成目标

【1】 Deziel, R.; Malenfant, E.; Inhibition of human cytomegalovirus protease N(o) with monocyclic beta-lactams. Bioorg Med Chem Lett 1998, 8, 11, 1437.

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)	30208	2-pyridinylmethanol；pyridin-2-ylmethanol；2-pyridylmethanol	586-98-1	C₆H₇NO	详情	详情
(II)	12893	Ethanethioic S-acid		C₂H₄OS	详情	详情
(III)	30209	S-(2-pyridinylmethyl) ethanethioate		C₈H₉NOS	详情	详情
(IV)	30210	4-oxo-2-azetidinyl acetate		C₅H₇NO₃	详情	详情
(V)	30211	4-[(2-pyridinylmethyl)sulfanyl]-2-azetidinone		C₉H₁₀N₂OS	详情	详情
(VI)	30212	1-[(1R)-1-isocyanatoethyl]benzene; (1R)-1-phenylethyl isocyanate	33375-06-3	C₉H₉NO	详情	详情

合成路线3

该中间体在本合成路线中的序号：(XV)

The precursor 3-chloro-4-(2-pyridylmethoxy)aniline (I) is prepared by coupling of 2-chloro-1-fluoro-4-nitrobenzene (XIV) with 2-pyridylmethanol (XV) by means of KOH in acetonitrile to give the 2-chloro-4-nitrophenyl ether (XVI) , which is then reduced to the corresponding aniline (I) by means of H2 over Pt/C or Pd/C in THF, or Zn and NH4Cl in EtOH .

参考文献中间体

合成目标

【3】 Rabindran, S.K., Tsou, H.-R., Wissner, A. (Wyeth). Protein tyrosine kinase enzyme inhibitors. US 2005059678, US 7399865, WO 2005028443.
【4】 Chew, W., Cheal, G.K., Lunetta, J.F. (Wyeth). Methods of synthesizing substituted 3-cyanoquinolines and intermediates thereof. EP 1883631, JP 2008545688, US 2006270668, WO 2006127207.
【1】 Chew, W., Papamichelakis, M. (Wyeth). Methods of preparing 3-cyanoquinolines and intermediates made thereby. WO 2006127205.
【2】 Wissner, A., Rabindran, S.K., Tsou, H.-R. (Wyeth). Substituted quinolines as protein tyrosine kinase enzyme inhibitors. EP 1670473, WO 2005034955.

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)	69190	3-Chloro-4-(2-pyridylmethoxy)aniline		C₁₂H₁₁ClN₂O	详情	详情
(XIV)	58441	2-chloro-1-fluoro-4-nitrobenzene; 3-Chloro-4-fluoronitrobenzene; 4-Fluoro-3-chloronitrobenzene	350-30-1	C₆H₃ClFNO₂	详情	详情
(XV)	30208	2-pyridinylmethanol；pyridin-2-ylmethanol；2-pyridylmethanol	586-98-1	C₆H₇NO	详情	详情
(XVI)	69201	2-((2-chloro-4-nitrophenoxy)methyl)pyridine;2-chloro-4-nitrophenyl ether		C₁₂H₉ClN₂O₃	详情	详情

Extended Information