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Potassium Carbonate → (R)-3-[2-Oxo-1-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-3-phenyl-propionic acid ethyl ester

HRID 2175186
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2175186
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]([NH:13][C:14]1[C:19]([N+:20]([O-])=O)=[CH:18][CH:17]=[C:16](C)[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].C[C:26]1[C:27]([CH3:42])=[C:28](C)[C:29]([CH3:40])=[C:30]2[C:34]=1[N:33]([CH3:35])[C:32](C)=[C:31]2[CH2:37]NI.[C:43]([O-])([O-])=[O:44].[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]([N:13]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:19]2[N:20]([CH2:37][C:31]2[C:30]3[C:34](=[CH:26][C:27]([CH3:42])=[CH:28][C:29]=3[CH3:40])[N:33]([CH3:35])[CH:32]=2)[C:43]1=[O:44])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 58497430(R)-3-(6-Methyl-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl esterHCID 131730211trimethyl-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-amino iodide

Produkt 1

HCID 58497410(R)-3-[2-Oxo-1-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-3-phenyl-propionic acid ethyl esterAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of (R)-3-(2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl)-3-phenyl-propionic acid ethyl ester (refer to example 2) (80 mg, 0.26 mmol) in DMF (10 mL) were added trimethyl-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-amino iodide (138 mg, 0.39 mmol) and K2CO3 (71 mg, 0.51 mmol) at room temperature. The solution was heated at 100° C. for 4 hours. The solution was cooled and was extracted with water and EtOAc. The combined organic layer was dried with MgSO4 and filtered. The filtrate was concentrated and the residue was purified by silica gel flash column chromatography with 20% EtOAc in Hexane as the eluent to afford the title compound (100 mg, 81%) as white foam.

Aufarbeitung

  1. temperatureThe solution was cooled
  2. extractionwas extracted with water and EtOAc
  3. dry with materialThe combined organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel flash column chromatography with 20% EtOAc in Hexane as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-3112dc9392224cd2b212d672e67debcc
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09062056B2

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