Sodium ethoxide → HCID 58336756, compound

HRID 2358978Notes

Reaction equation

HRID 2358978 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([C:12]3[N:17]=[C:16]([C:18]([NH2:20])=[NH:19])[CH:15]=[CH:14][CH:13]=3)[CH:9]=[N:8]2)[CH:2]=1.F[P-](F)(F)(F)(F)F.CN(C)[CH:30]=[CH:31][CH:32]=[N+](C)C.[O-]CC.[Na+]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([C:12]3[N:17]=[C:16]([C:18]4[N:20]=[CH:32][CH:31]=[CH:30][N:19]=4)[CH:15]=[CH:14][CH:13]=3)[CH:9]=[N:8]2)[CH:2]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 58336735HCID 58336735, compoundHCID 85361696HCID 85361696, compound

Product 1

HCID 58336756HCID 58336756, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Under argon, 0.73 g (2.7 mmol) of 6-(1-pyridin-3-yl-1H-pyrazol-4-yl)pyridine-2-carboxamidine and 0.8 g (2.9 mmol) of (3-dimethylaminoallylidene)dimethylammonium hexafluorophosphate in 30 ml of ethanol were heated under reflux with 3 ml of sodium ethoxide as a solution in ethanol (21%, corresponds to 8.1 mmol) for 6 h. The mixture was concentrated, Na citrate buffer, dil. aqueous sodium hydroxide solution to pH=9, aq. NaCl and ethyl acetate/THF were added, the aqueous phase was extracted three more times with dichloromethane/2-propanol and the combined organic phases were dried with MgSO4 and concentrated by evaporation. The residue was recrystallized from ethanol, during this operation, the mixture was briefly boiled with activated carbon and filtered whilst still hot, the filtrate was concentrated slightly and the precipitate formed was washed with MTBE and dried on a rotary evaporator. The residue was purified further by filtration through silica gel using acetone.

Workup

  1. concentrationThe mixture was concentrated
  2. additionNa citrate buffer, dil. aqueous sodium hydroxide solution to pH=9, aq. NaCl and ethyl acetate/THF were added
  3. extractionthe aqueous phase was extracted three more times with dichloromethane/2-propanol
  4. dry with materialthe combined organic phases were dried with MgSO4
  5. concentrationconcentrated by evaporation
  6. customThe residue was recrystallized from ethanol, during this operation
  7. filtrationfiltered whilst still hot, the filtrate
  8. concentrationwas concentrated slightly
  9. customthe precipitate formed
  10. washwas washed with MTBE
  11. customdried on a rotary evaporator
  12. filtrationThe residue was purified further by filtration through silica gel

Sources & evidence

ORD record
ord-0042691a926b4887a9681852676b25ae
Source dataset
uspto-grants-2014_04
Patent number
US08685964B2

Reaction notes

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