1H-Imidazole-2-carboxylicacid,1-methyl-4-[[(1-methyl-1H-imidazol-2- synthesis
- Product Name:1H-Imidazole-2-carboxylicacid,1-methyl-4-[[(1-methyl-1H-imidazol-2-
- CAS Number:464892-44-2
- Molecular formula:C10H11N5O3
- Molecular Weight:249.23
![1H-Imidazole-2-carboxylic acid, 1-methyl-4-[[(1-methyl-1H-imidazol-2-yl)carbonyl]amino]-, methyl ester](/CAS/20210305/GIF/849665-11-8.gif)
849665-11-8
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464892-44-2
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Yield:464892-44-2 82%
Reaction Conditions:
Stage #1: methyl 4-(N-methyl-1H-imidazole-2-carboxamido)-N-methyl-1H-imidazole-2-carboxylatewith sodium hydroxide in methanol;water at 50; for 12 h;
Stage #2: with hydrogenchloride in water at 0; pH=2;
Steps:
Methyl l-methyl-[4-(l-methyl-imidazole-2- carboxamido)]-imidazole-2-carboxylate 41 (3 g, 11.4 mmol) was dissolved in MeOH (75 mL). A solution of NaOH (2.3 g, 57 mmol) in H2O (75 mL) was added and the reaction mixture was allowed to stir at 50 °C for 12 h. Solvents were removed under reduced pressure and the residue was dissolved in H2O (25 mL). The solution was carefully acidified by dropwise addition of 2M HCl to pH 2 at 0 °C during which product precipitated. The solid was filtered washed with Et2O to furnish compound 44 (2.3 g, 82%). 1H-NMR (DMSO-d6) 610.13 (s, exch, IH, NH), 7.64 (s, IH, Im'- C5H), 7.49 (s, IH, Im-C5H), 7.09 (s, IH, Im-C3H), 3.99 (s, 3H, CH3), 3.93 (s, 3H, CH3). 13C-NMR (75 MHz, DMSO-de) 6159.9 (+, s, CO), 156.2 (+, s, CO), 137.8 (+, s, Im-C2), 135.9 (+, s, Im-C2), 132.6 (+, s, Im-C4), 127.8 (-, d, Im-C4), 127.1 (-, d, Im- C5), 115.2 (-, d, Im-C5), 35.9 (-, q, CH3), 35.3 (-, q, CH3). EI-HRMS: m/z calcd for Ci0HnN5O3 249.0862; found 205.0962 (M-CO2, 100%), 163.0965 (11%), 124.0511 (42%), 109.0401 (27%), 82.0524 (28%).
References:
WO2007/45096,2007,A1 Location in patent:Page/Page column 45; 89
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