Phenylacetyl chloride → 3-Benzyl-7-(4-bromo-2-chlorophenylamino)-8-chloro-[1,2,4]triazolo[4,3-a]pyridine-6-carboxylic acid methyl ester

Phenylacetyl chloride (152 μL, 1.148 mmol) was added to a solution of 4-(4-bromo-2-chlorophenylamino)-5-chloro-6-hydrazinonicotinic acid methyl ester (49) (0.233 g, 0.574 mmol) and triethylamine (160 μL, 1.148 mmol) in CH2Cl2 (5.7 mL) at 0° C. After warming to room temperature, an additional 75 μL phenylacetyl chloride was added. After 6 hours, the reaction mixture was concentrated and diluted with EtOAc. The organic layer was washed with water and brine, dried (Na2SO4) and concentrated. The residue (50b) was diluted with dichloroethylene (2 mL) and POCl3 (465 μL, 5.082 mmol) was added. After stirring at reflux for 12 hours, the reaction mixture was cooled to room temperature and concentrated. The residue was diluted with EtOAc and saturated NaHCO3 was added and the mixture stirred for 20 minutes. The resulting solid was collected by filtrate to give the desired product (51b) (97 mg, 30%).

1. concentrationthe reaction mixture was concentrated
2. additiondiluted with EtOAc
3. washThe organic layer was washed with water and brine
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated
6. additionwas added
7. temperatureat reflux for 12 hours
8. temperaturethe reaction mixture was cooled to room temperature
9. concentrationconcentrated
10. additionThe residue was diluted with EtOAc and saturated NaHCO3
11. additionwas added
12. stirringthe mixture stirred for 20 minutes
13. customThe resulting solid was collected by filtrate

ORDレコード

ord-382823a8a01f4526941ebb7d3f27f723

出典データセット

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07271178B2