5-FLUORO-1,3-DIHYDRO-BENZIMIDAZOL-2-ONE

General procedure: A typical procedure for the I-catalyzed reaction of aryl diamines with 1 atm COA stirred solution of 4-fluorobenzene-1 , 2-diamine (15.1 g, 120 mmol) in THF (120 mL) under nitrogen was cooled using an ice-bath and then was treated with di(1 -/-imidazol-1 - yl)methanone (23.4 g, 144 mmol) portion-wise over 15 min. The resulting mixture was slowly warmed to room temperature then was concentrated in vacuo after 2.5 h. The residue was suspended in a mixture of water and DCM (250 mL each) and filtered off. This residue was then washed with water (50 mL) and DCM (50 mL), before being dried at 40 °C under vacuum for 16 h to give the title compound (16.0 g, 105 mmol, 88percent) as a brown solid. LCMS (high pH): Rt 0.57 min; [M-HIntermediate 15: 5-Fluoro-1 , 3-dihvdro-2H-benzimidazol-2-one; A mixture of 4-fluoro-1 , 2-diaminobenzene (commercially available, 1.0 g, 7.9 mmol), carbonyldiimidazole (1.4 g) and THF (4 ml) was heated to 150 a) 4-Fluorobenzene-1, 2-diamine (2 g, 15.86 mmol) was dissolved in THF (49.4 ml) and 1, 1'-Carbonyldiimidazole (2.83 g, 17.44 mmol) was added at RT. The reaction mixture was stirred overnight at RT. To this was added concentrated ammonia solution (1.5 ml) and the mixture stirred for 30 minutes and then diluted with water (100 ml). The resultant solid was collected by filtration, washed with water, followed by Et[0278] To a solution of 4-fluorobenzene-1, 2-diamine lb (1.39 g, 11.0 mmol) and triethylamine (3.26 mE, 23.2 mmol) in methylene chloride (20 mE) was added dropwise a solution of diphosgene (0.69 mE, 5.72 mmol) in methylene chloride (5 mE) at 0 to 5° C. The resulting suspension was stirred for 2 hours at room temperature and filtered. The collected white solid was washed with water and dried to give compound 2b (1.56 g, 93percent). ‘H NMR (400 MHz, DMSO-d5) ö 10.73 (s, 1H), 10.61 (s, 1H), 6.97-6.81 (m, 1H), 6.74 (m, 2H); MS (ESI): mlz 153.1 [M+1]General procedure: To a solution of phthalic anhydride in THF (1.0 mm), TMSA (4.0 equiv.) was added and the mixture was refluxed with stirring for 30 h. The resulting solution was concentrated in vacuo until a solid formed. The solid was washed with diethyl ether (5×4 ml) to obtain high purity imidazolin-2‑ones 3.General procedure: A mixture of 2-phenoxycarbonyl-4, 5-dichloropyridazin-3(2H)-one (2a, 1.2 equiv), compounds 4 (1 equiv), and toluene (10 mL)was stirred at reflux conditions until amide intermediate wasconsumed (monitored by TLC). After cooling to r.t., the resultingprecipitate was filtered off and the solvent was evaporatedunder reduced pressure. The residue was transferred to anopen-bed silica gel column (3 × 7 cm). The column was elutedwith n-hexane–THF (1:2, v/v). Fractions containing compounds5 were combined and evaporated under reduced pressure togive compounds 5.

Molecular Weight:152.13
XLogP3:1.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:152.03859095
Monoisotopic Mass:152.03859095
Topological Polar Surface Area:41.1
Heavy Atom Count:11
Complexity:185
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes