反応 #607848

反応方程式

4-(4-amino-2-fluorophenoxy)-3-chloropicolinamide

1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid

EDCI

HOAT

→

title compound

収率 93.2%

3-chloro-4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)picolinamide

収率 93.2%

溶媒

DCM

反応条件

後処理

1. 1
   温度cooled to rt
2. 2
   その他quenched with 5 mL of water
3. 3
   抽出The mixture was extracted with EtOAc (10 mL×3)
4. 4
   洗浄the combined organic phases were washed with brine (10 mL×3)
5. 5
   乾燥dried over Na2SO4
6. 6
   濃縮concentrated in vacuo
7. 7
   その他The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=1/4)

実験手順

To a suspension of 4-(4-amino-2-fluorophenoxy)-3-chloropicolinamide (306 mg, 1.40 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (390 mg, 1.68 mmol) in DCM (6 mL) was added EDCI (322 mg, 1.68 mmol) and HOAT (38 mg, 0.28 mmol). The mixture was stirred at 45° C. for 14.5 hours, then cooled to rt and quenched with 5 mL of water. The mixture was extracted with EtOAc (10 mL×3) and the combined organic phases were washed with brine (10 mL×3), dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=1/4) to give the title compound as a pale yellow solid (647 mg, 93.2%).

出典