4-pyridinylmethanamine -Drug Synthesis Database

【结构式】

【分子编号】29396

【品名】4-pyridinylmethanamine

【CA登记号】3731-53-1

【分子式】C₆H₈N₂

【分子量】108.143

【元素组成】C 66.64% H 7.46% N 25.9%

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 intermediate monoprotected diaminopyridine (V) was prepared as shown in Scheme 1. After protection of 4-(aminomethyl)pyridine (I) as the tert-butyl carbamate (II) by means of Boc2O, reaction with peracetic acid yielded the corresponding pyridine N-oxide (III). Subsequent treatment of (III) with trimethylsilyl cyanide and dimethylcarbamyl chloride produced nitrile (IV), which was reduced to the required amine (V) by hydrogenation over Raney-Ni in the presence of ethanolic ammonia.

参考文献中间体

合成目标

【1】 Pasternak, A.; Chapman, K.; Guo, L.; Patchett, A.A.; Tata, J.R.; Yang, L. (Merck & Co., Inc.); Somatostatin agonists. EP 0977751; WO 9845285 .

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)	29396	4-pyridinylmethanamine	3731-53-1	C₆H₈N₂	详情	详情
(II)	29397	tert-butyl 4-pyridinylmethylcarbamate		C₁₁H₁₆N₂O₂	详情	详情
(III)	29398	4-[[(tert-butoxycarbonyl)amino]methyl]-1-pyridiniumolate		C₁₁H₁₆N₂O₃	详情	详情
(IV)	29399	tert-butyl (2-cyano-4-pyridinyl)methylcarbamate		C₁₂H₁₅N₃O₂	详情	详情
(V)	29400	tert-butyl [2-(aminomethyl)-4-pyridinyl]methylcarbamate		C₁₂H₁₉N₃O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XVI)

Palladium-catalyzed carbonylation of aryl triflate (XIV) under carbon monoxide atmosphere in the presence of methanol gave rise to the phenanthrenecarboxylate ester (XV). The ester group of (XV) was finally displaced with 4-(aminomethyl)pyridine (XVI) using trimethylaluminum catalyst to generate the target amide.

参考文献中间体

合成目标

【1】 Liu, K.K.-C.; Morgan, B.P.; Dow, R.L.; Swick, A.G. (Pfizer Inc.); Glucocorticoid receptor modulators. EP 1175383; WO 0066522 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIV)	51604	(4bS,7R,8aR)-4b-benzyl-7-hydroxy-7-(1-propynyl)-4b,5,6,7,8,8a,9,10-octahydro-2-phenanthrenyl trifluoromethanesulfonate		C₂₅H₂₅F₃O₄S	详情	详情
(XV)	51605	methyl (4bS,7R,8aR)-4b-benzyl-7-hydroxy-7-(1-propynyl)-4b,5,6,7,8,8a,9,10-octahydro-2-phenanthrenecarboxylate		C₂₆H₂₈O₃	详情	详情
(XVI)	29396	4-pyridinylmethanamine	3731-53-1	C₆H₈N₂	详情	详情

Extended Information