tert-butyl [2-(aminomethyl)-4-pyridinyl]methylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】29400

【品名】tert-butyl [2-(aminomethyl)-4-pyridinyl]methylcarbamate

【CA登记号】

【分子式】C₁₂H₁₉N₃O₂

【分子量】237.30188

【元素组成】C 60.74% H 8.07% N 17.71% O 13.48%

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)

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：(V)

Condensation of beta-methyl-D-tryptophan methyl ester (VI) with disuccinimidyl carbonate (VIII) and then with 4-(2-oxo-1-benzimidazolinyl) piperidine (VII) furnished urea (IX). Basic hydrolysis of the methyl ester of (IX), followed by coupling of the resulting carboxylic acid (X) with the intermediate amine (V) in the presence of EDC and HOBt yielded the corresponding amide (XI). The Boc protecting group of (XI) was finally cleaved with trifluoroacetic acid to give the title compound.

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
(V)	29400	tert-butyl [2-(aminomethyl)-4-pyridinyl]methylcarbamate		C₁₂H₁₉N₃O₂	详情	详情
(VI)	29274	methyl (2R,3S)-2-amino-3-(1H-indol-3-yl)butanoate		C₁₃H₁₆N₂O₂	详情	详情
(VII)	12138	1-(4-Piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one; 4-(2-Keto-1-benzimidazolinyl)piperidine	20662-53-7	C₁₂H₁₅N₃O	详情	详情
(VIII)	20417	1-([[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy)-2,5-pyrrolidinedione	74124-79-1	C₉H₈N₂O₇	详情	详情
(IX)	29401	methyl (2R,3S)-3-(1H-indol-3-yl)-2-([[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]carbonyl]amino)butanoate		C₂₆H₂₉N₅O₄	详情	详情
(X)	29402	(2R,3S)-3-(1H-indol-3-yl)-2-([[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]carbonyl]amino)butyric acid		C₂₅H₂₇N₅O₄	详情	详情
(XI)	29403	tert-butyl [2-([[(2R,3S)-3-(1H-indol-3-yl)-2-([[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]carbonyl]amino)butanoyl]amino]methyl)-4-pyridinyl]methylcarbamate		C₃₇H₄₄N₈O₅	详情	详情

Extended Information