Реакция #804197

Уравнение реакции

methyl 2-(3-fluorophenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

methanol

sodium hydroxide

→

2-(3-Fluorophenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid

Растворители

water

Условия реакции

Обработка

1. 1
   ДругоеInto a 50-mL round-bottom flask, was placed
2. 2
   КонцентрированиеThe resulting mixture was concentrated under vacuum
3. 3
   workup.ADDITIONThe resulting solution was diluted with 20 mL of H2O
4. 4
   ФильтрацияThe resulting solids were collected by filtration
5. 5
   ДругоеThe crude product (70 mg) was purified by Prep-HPLC with the following conditions (1#-Waters 2767-2)
6. 6
   workup.WAITup to 100% in 1.5 min)
7. 7
   ДругоеThis resulted in 20 mg (27%) of 2-(3-fluorophenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid as a yellow solid

Методика

Into a 50-mL round-bottom flask, was placed methyl 2-(3-fluorophenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (75 mg, 0.21 mmol, 1.00 equiv), methanol (15 mL), sodium hydroxide (42 mg, 1.05 mmol, 4.94 equiv), water (2 mL). The resulting solution was stirred for 2 hs at 50° C. in an oil bath. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 20 mL of H2O. The pH value of the aqueous solution was adjusted to 4-5 with aqueous hydrogen chloride (1 mol/L). The resulting solids were collected by filtration. The crude product (70 mg) was purified by Prep-HPLC with the following conditions (1#-Waters 2767-2): Column, SunFire Prep C18, 5 um, 19*150 mm; mobile phase, water with 0.05% TFA and CH3CN (50% CH3CN up to 80% in 8 min, up to 100% in 1.5 min); Detector, uv 220&254 nm. This resulted in 20 mg (27%) of 2-(3-fluorophenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid as a yellow solid.

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