Potassium Carbonate → 10-Methyl-6-oxo-7,8,9,10-tetrahydro-6H-pyrido[3',2':4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxylic acid

HRID 1521710Notes

Reaction equation

HRID 1521710 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([N:6]1[C:10]2=[N:11][C:12]([C:15]([O:17]CC)=[O:16])=[CH:13][CH:14]=[C:9]2[CH:8]=[C:7]1[C:20]([O:22]CC)=O)[CH3:5].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:5][CH:4]1[N:6]2[C:10]3[N:11]=[C:12]([C:15]([OH:17])=[O:16])[CH:13]=[CH:14][C:9]=3[CH:8]=[C:7]2[C:20](=[O:22])[NH:1][CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67237898Diethyl 1-(4-aminobutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

Product 1

HCID 6723721510-Methyl-6-oxo-7,8,9,10-tetrahydro-6H-pyrido[3',2':4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxylic acidYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of diethyl 1-(4-aminobutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (1.20 g, 3.60 mmol) in ethanol (35 mL) is added potassium carbonate (1.49 g, 10.8 mmol). The mixture is stirred at 60° C. for 16 h and is then cooled to room temperature. The ethanol is removed in vacuo and the aqueous mixture is acidified to pH 5 with 1N hydrochloric acid and is extracted with ethyl acetate. The combined organic phases are washed with brine, and are dried (Na2SO4) and concentrated in vacuo to afford the title compound as a yellow solid (500 mg, 54%). LCMS: (M+H+).

Workup

  1. temperatureis then cooled to room temperature
  2. customThe ethanol is removed in vacuo
  3. extractionis extracted with ethyl acetate
  4. washThe combined organic phases are washed with brine
  5. dry with materialare dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c047bfda447435b98bc523810be7759
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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