phenyl (1-methyl-5-(tritylamino)-1H-pyrazol-4-yl)carbamate -Drug Synthesis Database

【结构式】

【分子编号】69144

【品名】phenyl (1-methyl-5-(tritylamino)-1H-pyrazol-4-yl)carbamate

【CA登记号】　

【分子式】C₃₀H₂₆N₄O₂

【分子量】474.562

【元素组成】C 5675.93% H 5.52% N 11.81% O 6.74%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(X)

The pyrazolyl urea intermediate (IV) is prepared as follows. Treatment of 5-amino-1-methylpyrazole (VI) with NaNO2/HCl in water at 5 oC gives the 4-nitrosopyrazole derivative (VII), which is reduced to the diaminopyrazole (VIII) by catalytic hydrogenation over Pd/C in the presence of H2SO4. Selective acylation of the 4-amino group of compound (VIII) with phenyl chloroformate in the presence of NaOH in H2O/dioxane at 10 oC then yields the phenyl carbamate (IX). After protection of the free amine group of carbamate (IX) with chlorotriphenylmethane in the presence of Et3N in THF, the resulting N-trityl derivative (X) is coupled with N-Boc-ethylenediamine (XI) in the presence of Et3N in DMF to afford pyrazolyl urea (IV) .

参考文献中间体

合成目标

【1】 Ohki, H., Yamanaka, T., Toda, A. et al. (Astellas Pharma, Inc.; Wakunaga Pharmaceutical Co., Ltd.). Cephem compounds. EP 1556389, JP 2006506459, US 7129232, US 2007037786, WO 2004039814.
【2】 Toda, A., Ohki, H., Yamanaka, T. et al. Synthesis and SAR of novel parenteral anti-pseudomonal cephalosporins: Discovery of FR264205. Bioorg Med Chem Lett 2008, 18(17): 4849-52.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	69139	4-[(N-Boc-aminoethyl)carbamoylamino]-1-methyl-5-tritylaminopyrazole;tert-butyl (2-(3-(1-methyl-5-(tritylamino)-1H-pyrazol-4-yl)ureido)ethyl)carbamate		C₃₁H₃₆N₆O₃	详情	详情
(VI)	69140	1-methyl-1H-pyrazol-5-amine；1-Methyl-1H-pyrazol-5-ylamine	1192-21-8	C₄H₇N₃	详情	详情
(VII)	69141	1-methyl-4-nitro-1H-pyrazol-5-amine；5-Amino-1-methyl-4-nitropyrazole	19868-85-0	C₄H₆N₄O₂	详情	详情
(VIII)	69142	1-methyl-1H-pyrazole-4,5-diamine		C₄H₈N₄	详情	详情
(IX)	69143	phenyl (5-amino-1-methyl-1H-pyrazol-4-yl)carbamate		C₁₁H₁₂N₄O₂	详情	详情
(X)	69144	phenyl (1-methyl-5-(tritylamino)-1H-pyrazol-4-yl)carbamate		C₃₀H₂₆N₄O₂	详情	详情
(XI)	13241	N-Boc-ethylenediamine;tert-butyl (2-aminoethyl)carbamate；tert-butyl 2-aminoethylcarbamate; tert-Butyl n-(2-aminoethyl)carbamate	57260-73-8	C₇H₁₆N₂O₂	详情	详情

Extended Information