Methyl iodide → (R)-3-(sec-Butyl(methyl)amino)-2-phenylquinoxaline-6-carboxylic acid
Reaction equation
[C@H:1]([NH:5][C:6]1[C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:8][C:9]2[C:14]([N:15]=1)=[CH:13][C:12]([C:16]([O:18]C)=[O:17])=[CH:11][CH:10]=2)([CH2:3][CH3:4])[CH3:2].[H-].[Na+].[CH3:28]I>O1CCCC1>[C@H:1]([N:5]([CH3:28])[C:6]1[C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:8][C:9]2[C:14]([N:15]=1)=[CH:13][C:12]([C:16]([OH:18])=[O:17])=[CH:11][CH:10]=2)([CH2:3][CH3:4])[CH3:2]Participants
Procedure
Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of (R)-methyl 3-(sec-butylamino)-2-phenylquinoxaline-6-carboxylate (110 mg, 0.33 mmol, 1.00 equiv) in tetrahydrofuran (9 mL). sodium hydride (132 mg, 3.3 mmol, 10.00 equiv, 60%) was added. The resulting solution was stirred for 1 h at room temperature. This was followed by the dropwise addition of a solution of CH3I (922.5 mg, 6.50 mmol, 20.00 equiv) in tetrahydrofuran (2 mL) with stirring at 0° C. The resulting solution was stirred for overnight at 20° C. The resulting mixture was concentrated under vacuum and diluted by 10 ml of H2O. The pH value of the aqueous solution was adjusted to 3-4 with 1N hydrogen chloride. The resulting solid was collected by filtration. This resulted solid in 67 mg (59%) of (R)-3-(sec-butyl(methyl)amino)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid.
Workup
- customInto a 50-mL round-bottom flask purged
- temperaturemaintained with an inert atmosphere of nitrogen
- stirringwith stirring at 0° C
- stirringThe resulting solution was stirred for overnight at 20° C
- concentrationThe resulting mixture was concentrated under vacuum
- additiondiluted by 10 ml of H2O
- filtrationThe resulting solid was collected by filtration
Sources & evidence
- ORD record
- ord-59d76d8681864ff6a64d582cd7d04cc8
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916560B2
Reaction notes
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