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 2175186Notes

Reaction equation

HRID 2175186 reaction equation
[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]

Participants

5

Reactant 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

Product 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 esterYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3112dc9392224cd2b212d672e67debcc
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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