3-methoxy-2,6-dimethyl-4(1H)-pyridinone -Drug Synthesis Database

【结构式】

【分子编号】15908

【品名】3-methoxy-2,6-dimethyl-4(1H)-pyridinone

【CA登记号】

【分子式】C₈H₁₁NO₂

【分子量】153.18088

【元素组成】C 62.73% H 7.24% N 9.14% O 20.89%

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：(I)

The condensation of 3-methoxy-2,6-dimethylpyridin-4(1H)-one (I) with 5-[4'-(bromomethyl)biphenyl-2-yl]-1-(triphenylmethyl)tetrazole (II) by means of NaH in hot DMF gives the condensation product (III), which is finally deprotected by treatment with HCl in methanol/dichloromethane.

参考文献中间体

合成目标

【1】 Mealy, N.; Ngo, J.; Castaner, J.; ME-3221. Drugs Fut 1996, 21, 8, 794.
【2】 Katano, K.; Ogino, H.; Shitara, E.; Watanabe, H.; Nagura, J.; Osada, N.; Ichimaru, Y.; Konno, F.; Machinami, T.; Tsuruoka, T. (Meiji Seika Kaisha, Ltd.); Pyridine derivs. with angiotensin II antagonism. EP 0487745; US 5399566; WO 9119697 .

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)	15908	3-methoxy-2,6-dimethyl-4(1H)-pyridinone		C₈H₁₁NO₂	详情	详情
(II)	15538	5-[4'-(bromomethyl)[1,1'-biphenyl]-2-yl]-2-trityl-2H-1,2,3,4-tetraazole	124750-51-2	C₃₃H₂₅BrN₄	详情	详情
(III)	15910	2,6-dimethyl-4-[[2'-(1-trityl-1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methoxy]-3-pyridinyl methyl ether; 3-methoxy-2,6-dimethyl-4-[[2'-(1-trityl-1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methoxy]pyridine		C₄₁H₃₅N₅O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

Alkylation of L-cysteine (I) with cyclopentylmethyl methanesulfonate (II) produced the cysteine thioether (III). A tert-butoxycarbonyl group was subsequently introduced into the amino group of (III) by using di-tert-butyl dicarbonate and NaOH. The resultant N-Boc-cysteine thioether (V) was finally coupled with p-methoxybenzylamine (VI) by means of EDC and HOBt to furnish the corresponding amide.

参考文献中间体

合成目标

【1】 Seko, T.; et al.; Structure-activity study and analgesic efficacy of amino acid derivatives as N-type calcium channel blockers. Bioorg Med Chem Lett 2001, 11, 16, 2067.
【2】 Seko, T.; Kato, M. (Ono Pharmaceutical Co., Ltd.); Amino acid derivs.. EP 0997147; WO 9902146 .

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)	14643	L-cysteine; (R)-2-Amino-3-mercaptopropionic acid	52-90-4	C₃H₇NO₂S	详情	详情
(II)	51117	cyclopentylmethyl methanesulfonate		C₇H₁₄O₃S	详情	详情
(III)	51118	(2R)-2-amino-3-[(cyclopentylmethyl)sulfanyl]propionic acid		C₉H₁₇NO₂S	详情	详情
(IV)	51119	(2R)-2-[(tert-butoxycarbonyl)amino]-3-[(cyclopentylmethyl)sulfanyl]propionic acid		C₁₄H₂₅NO₄S	详情	详情
(V)	15908	3-methoxy-2,6-dimethyl-4(1H)-pyridinone		C₈H₁₁NO₂	详情	详情

Extended Information