Methanol → Quinoxaline-6-carboxylic acid
Reaction equation
FC1C=C([C:8]2[C:17](N(C(C)C)C)=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:23]([O:25]C)=[O:24])[CH:14]=3)[N:9]=2)C=CC=1.CO.[OH-].[Na+]>O>[N:9]1[C:10]2[C:15](=[CH:14][C:13]([C:23]([OH:25])=[O:24])=[CH:12][CH:11]=2)[N:16]=[CH:17][CH:8]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
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-(isopropylmethyl)amino)quinoxaline-6-carboxylic acid as a yellow solid.
Workup
- customInto a 50-mL round-bottom flask, was placed
- concentrationThe resulting mixture was concentrated under vacuum
- additionThe resulting solution was diluted with 20 mL of H2O
- filtrationThe resulting solids were collected by filtration
- customThe crude product (70 mg) was purified by Prep-HPLC with the following conditions (1#-Waters 2767-2)
- waitup to 100% in 1.5 min)
Sources & evidence
- ORD record
- ord-3afc64a9c54541bd98677c7ce7ce6943
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916560B2
Reaction notes
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