N,N'-Dimethylethylenediamine → HCID 89690318, compound

HRID 2202848Notes

Reaction equation

HRID 2202848 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6]3[CH:11]=[CH:10][C:9](I)=[CH:8][N:7]3[C:13]=2[CH3:14])[CH2:3][CH2:2]1.[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][NH:26][C:25](=[O:29])[CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.CS(C)=O>[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][N:26]([C:9]2[CH:10]=[CH:11][C:6]3[N:7]([C:13]([CH3:14])=[C:4]([CH:1]4[CH2:3][CH2:2]4)[N:5]=3)[CH:8]=2)[C:25](=[O:29])[CH:24]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 896903982-Cyclopropyl-6-iodo-3-methylimidazo[1,2-a]pyridine

Product 1

HCID 89690318HCID 89690318, compoundYield 55.6%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-cyclopropyl-6-iodo-3-methylimidazo[1,2-a]pyridine (1482 mg), 4-(benzyloxy)pyridin-2(1H)-one (1000 mg), copper iodide (946 mg), N,N′-dimethylethylenediamine (0.534 ml), potassium carbonate (2061 mg) and DMSO (13 ml) was heated 110° C. for 1 h under microwave irradiation. The residue was quenched with 28% NH3 solution, and extracted with EtOAc/THF. The organic layer was separated, washed with water and brine, dried over MgSO4, passed through silica gel pad (EtOAc only) and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/MeOH) and recrystallized from EtOH (80 ml) to give the title compound (1027 mg) as an off-white solid.

Workup

  1. customThe residue was quenched with 28% NH3 solution
  2. extractionextracted with EtOAc/THF
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (EtOAc/MeOH)
  8. customrecrystallized from EtOH (80 ml)

Sources & evidence

ORD record
ord-5300e863aff94155984dad8898271339
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

Loading…