反应 #1135889

反应方程式

NaOH

2-(methyl((3-((3-(trifluoromethyl)phenyl) ethynyl) imidazo[1,2-a]pyridin-2-yl)methyl)amino)acetate

methanol

acetic acid

NaOH

→

2-(methyl((3-((3-(trifluoromethyl)phenyl) ethynyl)imidazo[1,2-a]pyridin-2-yl)methyl)amino) acetic acid

收率 73.7%

溶剂

tetrahydrofurane

—

mixture

water

反应条件

后处理

1. 1
   workup.STIRRINGThe mixture was stirred at r.t. for 16 h
2. 2
   workup.STIRRINGThe mixture was stirred at r.t. for a further 24 h
3. 3
   workup.STIRRINGThe mixture was stirred at r.t. for 30 min
4. 4
   其他The solid formed
5. 5
   其他was isolated by filtration
6. 6
   洗涤washed with 5 ml of water
7. 7
   其他dried in a vacuum bell jar in order

实验过程

0.22 g (0.543 mmol) of 2-(methyl((3-((3-(trifluoromethyl)phenyl) ethynyl) imidazo[1,2-a]pyridin-2-yl)methyl)amino)acetate were dissolved in 6 ml of a mixture consisting of methanol and tetrahydrofurane with magnetic stirring and then 0.543 ml (0.543 mmol) of a 1M NaOH aqueous solution were added. The mixture was stirred at r.t. for 16 h. 0.163 ml (0.163 mmol) of a 1M NaOH aqueous solution were added. The mixture was stirred at r.t. for a further 24 h before being treated with a solution of 0.04 ml (0.705 mmol) of acetic acid in 10 ml of water. The mixture was stirred at r.t. for 30 min. The solid formed was isolated by filtration, washed with 5 ml of water and dried in a vacuum bell jar in order to obtain 0.155 g (yield=73%) of 2-(methyl((3-((3-(trifluoromethyl)phenyl) ethynyl)imidazo[1,2-a]pyridin-2-yl)methyl)amino) acetic acid as a beige solid. LC-MS: m/z=388 (MH+); UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 8.74 (d, J=6.7 Hz, 1H), 8.10 (s, 1H), 7.97 (d, J=7.6 Hz, 1H), 7.77 (d, J=7.8 Hz, 1H), 7.74-7.64 (m, 2H), 7.49-7.39 (m, 1H), 7.13 (t, J=6.4 Hz, 1H), 4.02 (s, 2H), 3.59 (s, 1H), 3.33 (s, 2H), 2.41 (s, 3H).

来源