Cesium carbonate → HCID 58577309, compound

HRID 82561

Reaction equation

HRID 82561 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:14]4=[N:15][CH:16]=[CH:17][CH:18]=[C:13]4[N:12]([CH2:19][CH3:20])[C:11]3=[O:21])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl[C:23]1[S:24][CH:25]=[CH:26][N:27]=1.C([O-])([O-])=O.[Cs+].[Cs+].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:19]([N:12]1[C:13]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[N:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[N:1]([C:23]2[S:24][CH:25]=[CH:26][N:27]=2)[CH:2]=[CH:3]3)[C:11]1=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 764292-ChlorothiazoleHCID 516892Sodium BicarbonateHCID 585772823-(2,3-dihydro-1H-indol-5-yl)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 58577309HCID 58577309, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(2,3-dihydro-1H-indol-5-yl)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (75 mg), 2-chlorothiazole (48.0 mg) and Cs2CO3 (174 mg) in DMF (3 mL) was stirred at 100° C. for 3 days, treated with saturated NaHCO3 solution, and extracted with AcOEt. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. The residue was purified by prep. HPLC and crystallized from AcOEt/Hexane to give the title compound as white crystals (27.0 mg).

Workup

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by prep
  6. customHPLC and crystallized from AcOEt/Hexane

Sources & evidence

ORD record
ord-a616ade2b40049af96929bb3f057c80d
Source dataset
uspto-grants-2014_09
Patent number
US08846713B2

Linked notes

Loading…