Potassium Carbonate → HCID 67325957, compound

HRID 871888Notes

Reaction equation

HRID 871888 reaction equation
[NH2:1][C:2]1[N:29]([CH2:30][C:31]([OH:34])([CH3:33])[CH3:32])[C:6]2[N:7]=[C:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([CH:18]4[CH2:23][CH2:22][N:21]([CH2:24][CH2:25]Cl)[CH2:20][CH2:19]4)=[CH:14][C:13]=3[O:27][CH3:28])[N:9]=[CH:10][C:5]=2[C:4](=[O:35])[C:3]=1[C:36]([NH2:38])=[O:37].[C:39]([O-])([O-])=[O:40].[K+].[K+]>CO>[NH2:1][C:2]1[N:29]([CH2:30][C:31]([OH:34])([CH3:33])[CH3:32])[C:6]2[N:7]=[C:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([CH:18]4[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][O:40][CH3:39])[CH2:20][CH2:19]4)=[CH:14][C:13]=3[O:27][CH3:28])[N:9]=[CH:10][C:5]=2[C:4](=[O:35])[C:3]=1[C:36]([NH2:38])=[O:37]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67325637HCID 67325637, compound

Product 1

HCID 67325957HCID 67325957, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 0.29 g (0.54 mmol) of the product prepared in step 22.1 in 9 mL of anhydrous methanol is added 0.37 g (2.68 mmol) of K2CO3, and the mixture is refluxed for 1 hour. It is evaporated to dryness and the residue is taken up in water and CH2Cl2. The organic phase is dried over MgSO4, filtered and concentrated under vacuum. The crude product is purified by chromatography on a column of silica, eluting with a dichloromethane/methanol gradient (90/10). After triturating in methanol, 0.22 g of the expected product is finally obtained in the form of a yellow solid. Yield=78%.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. customIt is evaporated to dryness
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude product is purified by chromatography on a column of silica
  7. washeluting with a dichloromethane/methanol gradient (90/10)
  8. customAfter triturating in methanol

Sources & evidence

ORD record
ord-314636aab22545fbbbbde962de208f22
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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