Potassium Carbonate → HCID 59447644, compound

HRID 1518360Notes

Reaction equation

HRID 1518360 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=[C:12]2[N:20](C(=O)C)[C:21](=[O:23])[CH3:22])=[CH:7][CH:6]=1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=[C:12]2[NH:20][C:21](=[O:23])[CH3:22])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59447637HCID 59447637, compound

Product 1

HCID 59447644HCID 59447644, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 77A (176 mg, 0.5 mmol) in MeOH (4 ml) was treated with K2CO3 (69.1 mg, 0.5 mmol) and stirred at ambient temperature for about 40 minutes. The reaction mixture was concentrated to remove MeOH, diluted with EtOAc and acidified to pH 5 with 1N HCl solution. The mixture was poured into a separatory funnel and the layers were separated. The aqueous layer was extracted with EtOAc (2×40 mL). The combined organic layers were dried (MgSO4), filtered and concentrated to provide the title compound 77B as an off-white solid in 67% yield: 1H NMR (300 MHz, DMSO-d6) δ ppm 10.26 (1H, s), 9.84 (1H, s), 7.63 (1H, m), 7.20 (5H, m), 6.93 (2H, m), 1.94 (3H, s).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove MeOH
  3. additiondiluted with EtOAc
  4. additionThe mixture was poured into a separatory funnel
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with EtOAc (2×40 mL)
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-fa8989f9351e4a4799b3dc31229e0c85
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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