tert-butyl 4-{[(3-amino-4-pyridinyl)amino]methyl}-1-piperidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】59461

【品名】tert-butyl 4-{[(3-amino-4-pyridinyl)amino]methyl}-1-piperidinecarboxylate

【CA登记号】

【分子式】C₁₆H₂₆N₄O₂

【分子量】306.4082

【元素组成】C 62.72% H 8.55% N 18.29% O 10.44%

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：(V)

4-(Aminomethyl)piperidine (I) was selectively protected at the piperidine N by means of Boc2O. The resultant 1-Boc-4-(aminomethyl)piperidine (II) was condensed with 4-chloro-3-nitropyridine (III) to afford the amino pyridine compound (IV). Catalytic hydrogenation of the nitro group of (IV) furnished the 3,4-diaminopyridine (V), which was cyclized with ethyl acetimidate hydrochloride (VI) to produce the imidazopyridine (VII). Subsequent acid cleavage of the Boc protecting group of (VII) provided the intermediate piperidine (VIII).

参考文献中间体

合成目标

【1】 Carceller, E.; Jimenez, P.J.; Salas, J.; Almansa, C.; Bartroli, J.; Merlos, M.; Giral, M.; Balsa, D.; Ferrando, R.; Garcia-Rafanell, J.; Forn, J. (J. Uriach & Cía., SA); Azo derivs. of 5-aminosalicylic acid for treatment of inflammatory bowel disease. EP 0790998; ES 2104513; ES 2106682; JP 1999501939; US 5747477; WO 9709329 .

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)	19349	4-piperidinylmethylamine; 4-piperidinylmethanamine; 4-(Aminomethyl)piperidine	7144-05-0	C₆H₁₄N₂	详情	详情
(II)	19352	4-Aminomethyl-1-N-Boc-piperidine; tert-butyl 4-(aminomethyl)-1-piperidinecarboxylate	144222-22-0	C₁₁H₂₂N₂O₂	详情	详情
(III)	29971	4-chloro-3-nitropyridine		C₅H₃ClN₂O₂	详情	详情
(IV)	59460	tert-butyl 4-{[(3-nitro-4-pyridinyl)amino]methyl}-1-piperidinecarboxylate		C₁₆H₂₄N₄O₄	详情	详情
(V)	59461	tert-butyl 4-{[(3-amino-4-pyridinyl)amino]methyl}-1-piperidinecarboxylate		C₁₆H₂₆N₄O₂	详情	详情
(VI)	12831	ethyl ethanimidoate	1000-84-6	C₄H₉NO	详情	详情
(VII)	59462	tert-butyl 4-[(2-methyl-1H-imidazo[4,5-c]pyridin-1-yl)methyl]-1-piperidinecarboxylate		C₁₈H₂₆N₄O₂	详情	详情
(VIII)	59463	2-methyl-1-(4-piperidinylmethyl)-1H-imidazo[4,5-c]pyridine		C₁₃H₁₈N₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

4-(Aminomethyl)piperidine (I) was selectively protected at the piperidine N by means of Boc2O. The resultant 1-Boc-4-(aminomethyl)piperidine (II) was condensed with 4-chloro-3-nitropyridine (III) to afford the amino pyridine compound (IV). Catalytic hydrogenation of the nitro group of (IV) furnished the 3,4-diaminopyridine (V), which was cyclized with ethyl acetimidate hydrochloride (VI), to produce the imidazopyridine (VII). Subsequent acid cleavage of the Boc protecting group of (VII) provided the intermediate piperidine (VIII).

参考文献中间体

合成目标

【1】 Carceller, E.; Jimenez, P.J.; Salas, J.; Almansa, C.; Bartroli, J.; Merlos, M.; Giral, M.; Balsa, D.; Ferrando, R.; Garcia-Rafanell, J.; Forn, J. (J. Uriach & Cía., SA); Azo derivs. of 5-aminosalicylic acid for treatment of inflammatory bowel disease. EP 0790998; ES 2104513; ES 2106682; JP 1999501939; US 5747477; WO 9709329 .

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)	19349	4-piperidinylmethylamine; 4-piperidinylmethanamine; 4-(Aminomethyl)piperidine	7144-05-0	C₆H₁₄N₂	详情	详情
(II)	19352	4-Aminomethyl-1-N-Boc-piperidine; tert-butyl 4-(aminomethyl)-1-piperidinecarboxylate	144222-22-0	C₁₁H₂₂N₂O₂	详情	详情
(III)	29971	4-chloro-3-nitropyridine		C₅H₃ClN₂O₂	详情	详情
(IV)	59460	tert-butyl 4-{[(3-nitro-4-pyridinyl)amino]methyl}-1-piperidinecarboxylate		C₁₆H₂₄N₄O₄	详情	详情
(V)	59461	tert-butyl 4-{[(3-amino-4-pyridinyl)amino]methyl}-1-piperidinecarboxylate		C₁₆H₂₆N₄O₂	详情	详情
(VI)	12831	ethyl ethanimidoate	1000-84-6	C₄H₉NO	详情	详情
(VII)	59462	tert-butyl 4-[(2-methyl-1H-imidazo[4,5-c]pyridin-1-yl)methyl]-1-piperidinecarboxylate		C₁₈H₂₆N₄O₂	详情	详情
(VIII)	59463	2-methyl-1-(4-piperidinylmethyl)-1H-imidazo[4,5-c]pyridine		C₁₃H₁₈N₄	详情	详情

Extended Information