反応 #91981

反応方程式

Methyl 3-amino-4-(4-cyano-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazol-5-yl)benzoate

HCl

dioxane

→

solid

収率 109.3%

Methyl 4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinoline-7-carboxylate

収率 109.3%

溶媒

ethyl acetate

反応条件

後処理

1. 1
   その他to give an orange solution
2. 2
   温度After 1 h at 90° C. the mixture was cooled to room temperature
3. 3
   濃縮concentrated in vacuo
4. 4
   その他to obtain a beige solid
5. 5
   洗浄washed with a mixture of water (100 mL) and saturated sodium bicarbonate solution (250 mL)
6. 6
   抽出The water phase was extracted with ethyl acetate (2×250 mL), organic phases
7. 7
   乾燥dried with MgSO4
8. 8
   濃縮concentrated in vacuo

実験手順

Methyl 3-amino-4-(4-cyano-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazol-5-yl)benzoate (2.79 g, 7.49 mmol) was combined with a solution of HCl in dioxane (4M, 56.2 mL, 225 mmol) to give an orange solution. The reaction mixture was heated to 90° C. under argon with stirring. After 1 h at 90° C. the mixture was cooled to room temperature and concentrated in vacuo to obtain a beige solid. The solid was dissolved in ethyl acetate (500 mL) washed with a mixture of water (100 mL) and saturated sodium bicarbonate solution (250 mL). The water phase was extracted with ethyl acetate (2×250 mL), organic phases were combined, dried with MgSO4 and concentrated in vacuo to obtain a yellow solid (3.05 g). The solid material was re-crystallized from ethyl acetate/heptane to give the title compound (2.4 g, 86%) as light yellow solid; LC-MS (UV peak area, ESI) 99%, 373.1884 (MH+).

出典