2-Bromo-4-(1-piperidinylmethyl)pyridine -Drug Synthesis Database

【结构式】

【分子编号】13021

【品名】2-Bromo-4-(1-piperidinylmethyl)pyridine

【CA登记号】

【分子式】C₁₁H₁₅BrN₂

【分子量】255.15758

【元素组成】C 51.78% H 5.93% Br 31.32% N 10.98%

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)

1) The reaction of 2-bromo-4-(piperidin-1-ylmethyl)pyridine (I) with 4-amino-2(Z)-buten-1-ol (II) by means of NaH in THF gives 4-[4-(piperidin-1-ylmethyl)pyridin-2-yloxy]-2(Z)-buten-1-amine (III), which is then condensed with 2-(2-furylmethylsulfinyl)acetic acid (IV) by means of 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide (EDCD) in dichloromethane.

参考文献中间体

合成目标

【1】 Hirakawa, N.; Kashiwaba, N.; Matsumoto, H.; Hosoda, A.; Sekine, Y.; Isowa, Y.; Yamaura, T.; Sekine, A.; Nishikawa, M. (UCB Japan); Pyridyloxy derivs. EP 0282077; JP 1988225371; JP 1989230556; JP 1989230576; US 4912101 .
【2】 Graul, A.; Prous, J.; Castaner, J.; Lafutidine. Drugs Fut 1994, 19, 9, 835.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	13021	2-Bromo-4-(1-piperidinylmethyl)pyridine	C₁₁H₁₅BrN₂	详情	详情
(II)	13022	(Z)-4-Amino-2-buten-1-ol	C₄H₉NO	详情	详情
(III)	13023	(Z)-4-[[4-(1-Piperidinylmethyl)-2-pyridinyl]oxy]-2-buten-1-amine; (Z)-4-[[4-(1-Piperidinylmethyl)-2-pyridinyl]oxy]-2-butenylamine	C₁₅H₂₃N₃O	详情	详情
(IV)	13024	2-[(2-Furylmethyl)sulfinyl]acetic acid	C₇H₈O₄S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

The condensation of 4-amino-2(Z)-buten-1-ol (I) with 2-bromo-4-(piperidinomethyl)pyridine (II) by means of NaH in refluxing THF gives 4-[4-(piperidinomethyl)pyridin-2-yloxy]-2(Z)-butenylamine (III), which is allowed to react with 3,4,-dimethoxy-3-cyclobutene-1,2-dione (IV) in methanol to afford 3-methoxy-4-[4-[4-(piperidinomethyl)pyridin-2-yloxy]-2(Z)-butenylamino]-3-cyclobutene-1,2-dione (V). Finally, this compound is treated with dry ammonia in methanol.

参考文献中间体

合成目标

【1】 Nohara, F.; Fujinawa, T. (Ikeda Mohando); Pyridyloxy derivs.. AU 8548136; EP 0177016; ES 8701161; JP 1986085365; JP 1986207375; JP 1991261766; US 4710498 .
【2】 Prous, J.; Castaner, J.; IT-066. Drugs Fut 1990, 15, 12, 1181.

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)	13022	(Z)-4-Amino-2-buten-1-ol		C₄H₉NO	详情	详情
(II)	13021	2-Bromo-4-(1-piperidinylmethyl)pyridine		C₁₁H₁₅BrN₂	详情	详情
(III)	13023	(Z)-4-[[4-(1-Piperidinylmethyl)-2-pyridinyl]oxy]-2-buten-1-amine; (Z)-4-[[4-(1-Piperidinylmethyl)-2-pyridinyl]oxy]-2-butenylamine		C₁₅H₂₃N₃O	详情	详情
(IV)	19999	3,4-dimethoxy-3-cyclobutene-1,2-dione	5222-73-1	C₆H₆O₄	详情	详情
(V)	31233	3-methoxy-4-[((Z)-4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-2-butenyl)amino]-3-cyclobutene-1,2-dione		C₂₀H₂₅N₃O₄	详情	详情

Extended Information