5-CARBOXYBENZIMIDAZOLONE METHYL ESTER

To a solution of 3, 4-diamino-benzoic acid methyl ester (5.00 g, 30.1 mmol) and THF (40 ml_), was added carbonyl diimidazole (7.32 g, 45.1 mmol) at 0 Methyl 3, 4-diaminobenzoate dihydrochloride (20 g, 0.08 mol) was mixed with urea (6.54 g, 0.11 mol). Reaction mixture was heated at 150° C. for 7 hours. After cooling powder was suspended in water (400 ml) and pH of the last one was adjusted to 0.45 with hydrochloric acid. Precipitate was filtered and rinsed with water and hydrochloric acid (pH=1.5). Obtained filter cake was dried at 100° C. Yield 15.7 g (97percent).Take 2-oxo-2, 3-dihydro-1H-benzo [d] imidazole-5-carboxylic acid methyl ester (1g, 5.2mmol), add it to the eggplant-shaped bottle, and then add DMF, Add sodium hydride (0.2 g, 10.4 mmol) under ice bath, After stirring for half an hour, potassium iodide (1.8 g, 13.0 mmol) was added dropwise to react at room temperature for 5 hours;After the reaction, add water, extract with dichloromethane, wash with brine, dry the organic layer, recrystallize, suction filter, and dry the filter cake under infrared.A white solid was obtained with a yield of 64%.To a stirred suspension of methyl 2-oxo-2, 3-dihydro-lH-benzo[d]imidazole-5- carboxylate57 (100 mg) and l-benzylpiperidin-4-amine181 (119 mg) in toluene (2 ml) under argon was added dropwise trimethylaluminum (520 mu, 2 M solution in toluene) to give a brown solution. The reaction mixture was stirred at 110 C for 2 h. LC-MS analysis indicated that the reaction was complete. The reaction mixture was quenched by dropwise addition to water (10 ml). THF (50 ml) was then added. The resulting mixture was stirred at room temperature for 1 h. The mixture was then washed twice with saturated brine. The organic layer was dried over Na2S04 and concentrated in vacuo. The crude material was triturated in EtOAc (4 ml), then filtered through sintered glass, washing with EtOAc (2 x) and then with Et20 (2 x). The solid crystals were dried in vacuo to afford 124 mg of an off-white solid. The impure solid was triturated with methanol (5 ml), then filtered through sintered glass, washing with methanol (1 x), and then with Et20 (2 x). The crystalline product was dried in vacuo to afford N-(l- benzylpiperidin-4-yl)-2-oxo-2, 3-dihydro-lH-benzo[d]imidazole-5-carboxamide (83 mg, 46%) as a white solid. MS (ISP): 351.1 ([M+H]+).

Molecular Weight:192.17
XLogP3:0.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:192.05349212
Monoisotopic Mass:192.05349212
Topological Polar Surface Area:67.4
Heavy Atom Count:14
Complexity:267
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes