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

HRID 1521705Notes

Reaction equation

HRID 1521705 reaction equation
[NH2:1][CH2:2][C:3]([CH3:25])([CH3:24])[CH2:4][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].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:24][C:3]1([CH3:25])[CH2:4][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][CH2:2]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67237221Diethyl 1-(3-amino-2,2-dimethylpropyl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

Product 1

HCID 672363209,9-Dimethyl-6-oxo-7,8,9,10-tetrahydro-6H-pyrido[3',2':4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxylic acidYield 107.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of diethyl 1-(3-amino-2,2-dimethylpropyl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (3.30 g, 9.50 mmol) in ethanol (45 mL) is added potassium carbonate (3.94 g, 28.5 mmol). The mixture is stirred at 60° C. for 16 h and is then cooled to room temperature. The ethanol is evaporated and the aqueous mixture is acidified to pH 5 with 1N hydrochloric acid. The resulting solid is collected by filtration and dried in vacuo to afford the title compound as a pale yellow solid (2.80 g, quantitative). LCMS: 274.70 (M+H+).

Workup

  1. temperatureis then cooled to room temperature
  2. customThe ethanol is evaporated
  3. filtrationThe resulting solid is collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-8be426d15cda4930a2f8caf613ca7a14
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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