Water → 2-(1,3-benzothiazol-2-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid

HRID 1403418Notes

Reaction equation

HRID 1403418 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:19]([N:20]2[CH2:24][CH2:23][CH2:22][C@@H:21]2[CH3:25])=[N:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:26]([O:28]C)=[O:27])[CH:16]=2)[N:11]=1.[OH-].[Na+].O>O1CCCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:19]([N:20]2[CH2:24][CH2:23][CH2:22][C@@H:21]2[CH3:25])=[N:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:26]([OH:28])=[O:27])[CH:16]=2)[N:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70664720methyl 2-(1,3-benzothiazol-2-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate

Product 1

HCID 706649952-(1,3-benzothiazol-2-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acidYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(1,3-benzothiazol-2-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate (80 mg, 0.20 mmol) in tetrahydrofuran (20 mL) was added NaOH (23.8 mg, 0.60 mmol) and water (1 mL). The resulting solution was stirred overnight at room temperature and then concentrated in vacuo, adjusted the pH to 7 with HCl (3 N). The product was collected and filtered to afford 2-(1,3-benzothiazol-2-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid as a light yellow solid (43.8 mg, 57%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe product was collected
  3. filtrationfiltered

Sources & evidence

ORD record
ord-2d61fbdcddc74a90841aefebcde647de
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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