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With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 1h;
A slurry of the 1 -methyl imidazol-4-yl acid (10 g, 79.3 mmol) iin dry DCM (100 ml) at room temperature was treated with dropwise addition of oxalyl chlodide ( 12 ml, mmol) and catalytic DMF ( pipette drops). The reaction bubbled immediately and the slurry was stirred for 1 hr. Removal of the solvent in vacuo followed by drying under high vacuum gave the title compound (9.1 g) as a tan white solid. 1H NMR (400MHz, MD3OD) delta. 9.09 (s, 1H), 8.24 (s, 1H), 3.98 (s, 3H).
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 25℃; for 48h;
Preparation of Compound 69aAt 0° C., a suspension of <strong>[41716-18-1]1-<strong>[41716-18-1]methyl-1H-imidazole-4-carboxylic acid</strong></strong> (100.9 mg, 0.8 mmol) in CH2Cl2 (8 mL) was added oxalylchloride (305 mg, 0.21 mL, 2.4 mmol) followed by addition of 1 drop of DMF. The mixture was stirred for 2 days at 25° C. All solvent was removed in vacuo to give a crude 69a.
With oxalyl dichloride;N,N-dimethyl-formamide; In chloroform; at 20℃; for 2h;Inert atmosphere;
Example 9Methyl N-[(1-methyl-1H-imidazol-4-yl)carbonyl]-N-(tetrahydro-2H-pyran-4-yl)-3-(trifluoromethoxy)phenylalaninate To a mixture of <strong>[41716-18-1]1-<strong>[41716-18-1]methyl-1H-imidazole-4-carboxylic acid</strong></strong> (500 mg) and chloroform (5 mL), oxalyl chloride (0.6 mL) was added in a nitrogen atmosphere. A drop of DMF was added to the resulting mixture, which was stirred for 2 hours at room temperature. The reaction mixture was concentrated under reduced pressure to give a solid (670 mg). The solid (31 mg) was added to methyl N-(tetrahydro-2H-pyran-4-yl)-3-(trifluoromethoxy)phenylalaninate (50 mg), diisopropylethylamine (51 muL) and chloroform (0.5 mL) and the resulting mixture was stirred for 12 hours at room temperature. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by column chromatography (NH silica gel cartridge; hexane/ethyl acetate=95:5 to 0:100) to give the titled compound (19 mg).
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