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

HRID 1521725Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521725
[NH2:1][CH2:2][C@@H: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]([O:21]CC)=O)[CH3:4].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:4][C@H:3]1[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:21])[NH:1][CH2:2]1

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 67236980Diethyl 1-[(2S)-1-aminopropan-2-yl]-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

Produkt 1

HCID 67236368(R)-9-methyl-6-oxo-6,7,8,9-tetrahydropyrido[3',2':4,5]pyrrolo[1,2-a]pyrazine-2-carboxylic acidAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of diethyl 1-[(2S)-1-aminopropan-2-yl]-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (2.17 g, 6.80 mmol) in ethanol (40 mL) is added potassium carbonate (2.82 g, 20.4 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 aqueous hydrochloric acid. The resulting solid is collected by filtration and dried in vacuo to afford the title compound as a pale yellow solid (1.40 g, 84%). LCMS: 246.64 (M+H+).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ea1b68ea6c25448b91fb878428516378
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073926B2

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