反応 #956989

反応方程式

1-(2-(benzyloxy)phenyl)cyclopropanamine

3-(3,5-dibromo-2-oxo-2H-pyrazin-1-yl)-5-fluoro-4-methyl-benzoic acid, methyl ester

N-ethyldiisopropylamine

→

subtitle compound

3-[5-bromo-2-oxo-3-[[1-[2-(phenylmethoxy)phenyl]cyclopropyl]amino]-1(2H)-pyrazinyl]-5-fluoro-4-methyl-benzoic acid, methyl ester

溶媒

dioxane

HCl

反応条件

後処理

1. 1
   その他The cooled reaction mixture
2. 2
   抽出extracted with ether (3×300 mL)
3. 3
   乾燥The combined organics were dried (MgSO4)
4. 4
   ろ過filtered
5. 5
   その他evaporated
6. 6
   その他to afford crude product
7. 7
   その他Purification (SiO2 chromatography eluting with 20% ethyl acetate in iso-hexane)

実験手順

A solution of 1-(2-(benzyloxy)phenyl)cyclopropanamine (Preparation 1h, 5 g) in dioxane (200 mL) was treated with 3-(3,5-dibromo-2-oxo-2H-pyrazin-1-yl)-5-fluoro-4-methyl-benzoic acid, methyl ester (Preparation 1g, 7.5 g) and N-ethyldiisopropylamine (5.36 mL) under nitrogen. The resulting solution was stirred at 100° C. for 8 h. The cooled reaction mixture was diluted with 2M HCl (300 mL), and extracted with ether (3×300 mL). The combined organics were dried (MgSO4), filtered and evaporated to afford crude product. Purification (SiO2 chromatography eluting with 20% ethyl acetate in iso-hexane) gave the subtitle compound. (9.20 g).

出典