ethyl 5-(chlorosulfonyl)-2-ethoxynicotinate -Drug Synthesis Database

【结构式】

【分子编号】62096

【品名】ethyl 5-(chlorosulfonyl)-2-ethoxynicotinate

【CA登记号】

【分子式】C₁₀H₁₂ClNO₅S

【分子量】293.72772

【元素组成】C 40.89% H 4.12% Cl 12.07% N 4.77% O 27.24% S 10.92%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(VI)

Reaction of 2-chloronicotinic acid (I) with an ethanolic solution of potassium tert-butoxide affords 2-ethoxynicotinic acid (II), which is further converted to the corresponding ethyl ester (III) by alkylation with iodoethane in the presence of Cs2CO3. Nitration of (III) employing ammonium nitrate and trifluoroacetic anhydride leads to ethyl 2-ethoxy-5-nitropyridine-3-carboxylate (IV). This is then reduced to the aminopyridine (V) by catalytic hydrogenation over Raney Ni. Diazotization of amine (V), followed by treatment with SO2 and CuCl2 gives rise to the sulfonyl chloride (VI). Acid chloride (VI) is subsequently coupled to N-ethylpiperazine (VII), producing sulfonamide (VIII). Alkaline hydrolysis of ethyl ester (VIII) yields the intermediate pyridinecarboxylic acid (IX)

参考文献中间体

合成目标

【1】 Street, S.D.A.; Wood, A.; Bunnage, M.E.; Mathias, J.P. (Pfizer Inc.; Pfizer Ltd.); Pyrazolopyrimidinone cGMP PDE5 inhibitors for the treatment of sexual dysfunction. WO 9954333 .

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)	28827	2-(2-chloroethyl)-4-methyl-3,4-dihydropyrido[3,2-f][1,4]oxazepine-5(2H)-thione		C₁₁H₁₃ClN₂OS	详情	详情
(II)	62092	2-ethoxynicotinic acid		C₈H₉NO₃	详情	详情
(III)	62093	ethyl 2-ethoxynicotinate		C₁₀H₁₃NO₃	详情	详情
(IV)	62094	ethyl 2-ethoxy-5-nitronicotinate		C₁₀H₁₂N₂O₅	详情	详情
(V)	62095	ethyl 5-amino-2-ethoxynicotinate		C₁₀H₁₄N₂O₃	详情	详情
(VI)	62096	ethyl 5-(chlorosulfonyl)-2-ethoxynicotinate		C₁₀H₁₂ClNO₅S	详情	详情
(VII)	14213	N-Ethylpiperazine; 1-Ethylpiperazine	5308-25-8	C₆H₁₄N₂	详情	详情
(VIII)	62097	ethyl 2-ethoxy-5-[(4-ethyl-1-piperazinyl)sulfonyl]nicotinate		C₁₆H₂₅N₃O₅S	详情	详情
(IX)	62098	2-ethoxy-5-[(4-ethyl-1-piperazinyl)sulfonyl]nicotinic acid		C₁₄H₂₁N₃O₅S	详情	详情

Extended Information