Hydrochloric Acid → HCID 86683687, compound

Temperature

140 °C

Glycine (80 mg, 1.07 mmol) and K2CO3 (207 mg, 1.5 mmol) were added to solution of 4-iodo-N-methyl-2-fluorobenzamide (279 mg, 1 mmol) in DMF (3 ml). The reaction mixture was stirred at 140° C. for 18 min. in microwave oven, cooled, diluted with AcOEt (10 ml) and water (10 ml), neutralized with HCl to pH 2-3, organic layer was separated, water layer was extracted with AcOEt (5×20 ml). The combined extracts were washed with brine, dried over Na2SO4 and evaporated in vacuo. The product was isolated by column chromatography on SiO2. It gave N-(4-methylcarbamoyl-2-fluorophenyl)glycine 4.2(1) (R1=CH3, R4=R5=H,). A solution of N-(4-methylcarbamoyl-2-fluorophenyl)glycine 4.2(1) (113 mg, 0.5 mmol) and 4-isothiocyanato-2-(trifluoromethyl)benzonirile 3.2 (174 mg, 1.0 mmol) in DMF (2 ml) was stirred at 90° C. for 12 h. The reaction mixture was evaporated in vacuo, and N-methyl-4-{4-oxo-2-thioxo-3-[3-(trifluoromethyl)-4-cyanophenyl]-imidazolidin-1-yl}-2-fluorobenzamide 1.2(1), was isolated by HPLC method, LCMS (M+H)+437.

1. temperaturecooled
2. customwas separated
3. extractionwater layer was extracted with AcOEt (5×20 ml)
4. washThe combined extracts were washed with brine
5. dry with materialdried over Na2SO4
6. customevaporated in vacuo
7. customThe product was isolated by column chromatography on SiO2

ORD record

ord-3974c5b18acf48858f0816190bb13287

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085539B2