Potassium Carbonate → 8,9-Dimethyl-6-oxo-6,7,8,9-tetrahydropyrido[3',2':4,5]pyrrolo[1,2-a]pyrazine-2-carboxylic acid

HRID 1521715Notes

Reaction equation

HRID 1521715 reaction equation
[NH2:1][CH:2]([CH3:24])[CH:3]([N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16]CC)=[O:15])=[CH:12][CH:13]=[C:8]2[CH:7]=[C:6]1[C:19](OCC)=[O:20])[CH3:4].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:24][CH:2]1[CH:3]([CH3:4])[N:5]2[C:9]3[N:10]=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=[CH:13][C:8]=3[CH:7]=[C:6]2[C:19](=[O:20])[NH:1]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67236563Diethyl 1-(3-aminobutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

Product 1

HCID 672367048,9-Dimethyl-6-oxo-6,7,8,9-tetrahydropyrido[3',2':4,5]pyrrolo[1,2-a]pyrazine-2-carboxylic acidYield 67.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of diethyl 1-(3-aminobutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (3.83 g, 11.5 mmol) in ethanol (45 mL) is added potassium carbonate (4.76 g, 34.5 mmol). The mixture is stirred at room temperature for 64 h. The ethanol is removed in vacuo and the aqueous mixture is acidified to pH 6 with 1N aqueous HCl. The resulting solid is collected by filtration and dried in vacuo to afford the title compound as a white solid (2.00 g, 54%). LCMS: 260.67 (M+H+).

Workup

  1. customThe ethanol is removed in vacuo
  2. filtrationThe resulting solid is collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-8078cfd1d8c54160b772a85dba85611c
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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