Potassium Carbonate → AZ4800

HRID 1930716Notes

Reaction equation

HRID 1930716 reaction equation
[CH:1]1([O:6][CH2:7][C:8]([CH:10]2[C:15](=O)[CH2:14][CH2:13][O:12][CH2:11]2)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([NH:31][C:32]([NH2:34])=[NH:33])[CH:22]=[CH:23][C:24]=1[N:25]1[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]1.C(=O)([O-])[O-].[K+].[K+]>CCO>[CH:1]1([O:6][CH2:7][C:8]2[C:10]3[CH2:11][O:12][CH2:13][CH2:14][C:15]=3[N:34]=[C:32]([NH:31][C:21]3[CH:22]=[CH:23][C:24]([N:25]4[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]4)=[C:19]([O:18][CH3:17])[CH:20]=3)[N:33]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 593337153-(2-(Cyclopentyloxy)acetyl)dihydro-2H-pyran-4(3H)-oneHCID 178493227HCID 178493227, compound

Product 1

HCID 50996844AZ4800Yield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(2-(Cyclopentyloxy)acetyl)dihydro-2H-pyran-4(3H)-one (280 mg, 1.24 mmol), 1-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)guanidine (1 equiv.) and potassium carbonate (2 equiv.) were heated to 50° C. over night in EtOH (5 mL). The crude product was extracted into DCM, the organic phase collected and solvent evaporated. The crude product was purified by flash chromatography (0-100% EtOAc in Heptane). The purity was not satisfactory so further purification on prepHPLC was performed to afford the title compound (83 mg, 16% yield).

Workup

  1. extractionThe crude product was extracted into DCM
  2. customthe organic phase collected
  3. customsolvent evaporated
  4. customThe crude product was purified by flash chromatography (0-100% EtOAc in Heptane)
  5. customThe purity was not satisfactory so further purification on prepHPLC

Sources & evidence

ORD record
ord-91b6065a47484265b414c30a0e697034
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

Loading…