5-(PYRIDIN-2-YLCARBAMOYL)-3 H-IMIDAZOLE-4-CARBOXYLIC ACID synthesis

Yield:436088-75-4 67%

Reaction Conditions:

Stage #1: 2-aminopyridine;5,10-dioxo-5H,10H-diimidazolo[1,5-a:1',5'-d]pyrazine-1,6-dicarboxylic acid diphenyl ester in tetrahydrofuran at 0 - 20; for 18.2 h;
Stage #2: with potassium hydroxide in methanol at 0 - 20; for 8.17 h;

Steps:

7 6.5.7 4-(Pyridin-2-ylcarbamoyl)-1H-imidazole-5-carboxylic acid (5)

General procedure: The title compound was obtained from 17 (100 mg, 0.233 mmol) and 2-aminopyridine (84 mg, 0.466 mmol) as described above in the method B. Pale yellow solid, yield 67%; ¹H NMR (300MHz, DMSO-d₆) δ 8.281(s, 1H), 7.844(d, J=11.7, 2H), 7.411(d, J=11.7, 2H); ¹³C NMR (100MHz, DMSO-d₆) δ 160.4, 150.7, 148.4, 138.5, 137.6, 137.5, 135.6, 129.8, 120.5, 114.4; ESI-MS: 233 [M+1]⁺; HRESI-MS: m/z calcd for C₁₀H₉N₄O₃ ([M+H]⁺) 233.0675; found 233.0690.

References:

Serrao, Erik;Xu, Zhong-Liang;Debnath, Bikash;Christ, Frauke;Debyser, Zeger;Long, Ya-Qiu;Neamati, Nouri [Bioorganic and Medicinal Chemistry,2013,vol. 21,# 19,p. 5963 - 5972]