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【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

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.

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 CAS号 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.

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