反応 #41792

反応方程式

3-(trifluoromethylthio)phenylisothiocyanate

4-(3-amino-4-methylamino-phenoxy)-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide

→

4-[1-Methyl-2-(3-trifluoromethylsulfanyl-phenylamino)-1H-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide

溶媒

MeOH

反応条件

後処理

1. 1
   その他The reaction was partitioned with EtOAc and water
2. 2
   ろ過filtered through Celite
3. 3
   その他The layers were separated
4. 4
   抽出The resulting aqueous phase was extracted with EtOAc
5. 5
   ろ過the mixture was filtered through Celite
6. 6
   その他The phases were separated
7. 7
   抽出the aqueous phase was again extracted
8. 8
   ろ過filtered
9. 9
   洗浄The combined organic layers were washed with brine
10. 10
    乾燥dried (MgSO4)
11. 11
    ろ過filtered
12. 12
    濃縮concentrated
13. 13
    その他to give a brown solid
14. 14
    その他The crude residue was purified by reverse phase HPLC

実験手順

A flask was charged with 3-(trifluoromethylthio)phenylisothiocyanate (1 eq), 4-(3-amino-4-methylamino-phenoxy)-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide (1 eq), and MeOH. The reaction was maintained at rt overnight. Ferric chloride, (1.5 eq) was added and the resulting red reaction mixture was stirred overnight. The reaction was partitioned with EtOAc and water, and filtered through Celite. The layers were separated and the aqueous phase was neutralized with saturated Na2CO3 solution. The resulting aqueous phase was extracted with EtOAc and the mixture was filtered through Celite. The phases were separated and the aqueous phase was again extracted and filtered. The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated to give a brown solid. The crude residue was purified by reverse phase HPLC. LCMS m/z 504.1 (MH+), tR=3.7 min.

出典