5-Amino-3-tert-butyl-1-methylpyrazole -Drug Synthesis Database

【结构式】

【分子编号】51506

【品名】5-Amino-3-tert-butyl-1-methylpyrazole

【CA登记号】118430-73-2

【分子式】C₈H₁₅N₃

【分子量】153.22732

【元素组成】C 62.71% H 9.87% N 27.42%

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：(IV)

4-(4-Pyridinylmethyl)aniline (II) was prepared by catalytic hydrogenation of the corresponding nitro derivative (I) over Pd/C. Condensation of aniline (II) with N,N'-carbonyldiimidazole produced the imidazolide (III). This was then condensed with 5-amino-3-tert-butyl-1-methylpyrazole (IV) to furnish the target urea.

参考文献中间体

合成目标

【1】 Riedl, B.; Lee, W.; Lowinger, T.B.; Redman, A.; Smith, R.A.; Khire, U.; Dumas, J.; Scott, W.J.; Wood, J.E.; Johnson, J.; Paulsen, H.; Hatoum-Mokdad, H. (Bayer Corp.); Inhibition of p38 kinase activity using substd. heterocyclic ureas. WO 9932111 .
【2】 Redman, A.; Paulsen, H.; Lowinger, T.B.; Dumas, J.; Johnson, J.; Wood, J.E.; Scott, W.J.; Khire, U.; Hatoum-Mokdad, H.; Lee, W.; Smith, R.A.; Riedl, B. (Bayer Corp.); Inhibition of raf kinase using substd. heterocyclic ureas. EP 1047418; WO 9932106 .

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)	51503	4-(4-Nitrobenzyl)pyridine; 4-(p-nitrobenzyl) pyridine	1083-48-3	C₁₂H₁₀N₂O₂	详情	详情
(II)	51504	4-(4-pyridinylmethyl)aniline; 4-(4-pyridinylmethyl)phenylamine		C₁₂H₁₂N₂	详情	详情
(III)	51505	N-[4-(4-pyridinylmethyl)phenyl]-1H-imidazole-1-carboxamide		C₁₆H₁₄N₄O	详情	详情
(IV)	51506	5-Amino-3-tert-butyl-1-methylpyrazole	118430-73-2	C₈H₁₅N₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The cyclization of 2-pivaloylacetonitrile (I) with methylhydrazine (II) in refluxing ethanol gives 5-amino-3-tert-butyl-1-methylpyrazole (III), which is finally condensed with 4-(4-pyridylmethyl)aniline (IV) and carbonyldimidazole (CDI) in dichloromethane to afford the target urea. The aniline (IV) has been obtained by reduction of the corresponding nitro derivative (V) with H2 over Pd/C in ethanol.

参考文献中间体

合成目标

【1】 Dumas, J.; et al.; Synthesis and pharmacological characterization of a potent, orally active p38 kinase inhibitor. Bioorg Med Chem Lett 2002, 12, 12, 1559.

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)	44248	4,4-dimethyl-3-oxopentanenitrile	59997-51-2	C₇H₁₁NO	详情	详情
(II)	12091	1-Methylhydrazine; Monomethyl hydrazine	60-34-4	CH₆N₂	详情	详情
(III)	51506	5-Amino-3-tert-butyl-1-methylpyrazole	118430-73-2	C₈H₁₅N₃	详情	详情
(IV)	51504	4-(4-pyridinylmethyl)aniline; 4-(4-pyridinylmethyl)phenylamine		C₁₂H₁₂N₂	详情	详情
(V)	51503	4-(4-Nitrobenzyl)pyridine; 4-(p-nitrobenzyl) pyridine	1083-48-3	C₁₂H₁₀N₂O₂	详情	详情

Extended Information