p-Toluenesulfonic acid → HCID 59280191, compound

HRID 1913196Notes

Reaction equation

HRID 1913196 reaction equation
CN(C)[CH:3]=[C:4]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[C:5](OCC)=[O:6].[NH:17]([C:19]1[N:24]=[CH:23][C:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:21][CH:20]=1)[NH2:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[O:6]=[C:5]1[N:17]([C:19]2[N:24]=[CH:23][C:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:21][CH:20]=2)[NH:18][CH:3]=[C:4]1[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 45089857Tert-butyl 6-hydrazinylpyridine-3-carboxylateHCID 687048643-(Dimethylamino)-2-pyridin-3-yl-acrylic acid ethyl ester

Product 1

HCID 59280191HCID 59280191, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

2.2 g (10.0 mmol) of the compound from Example 2A are initially charged in 50 ml of ethanol. 2.1 g (10.0 mmol) of the compound from Example 15A and 380 mg (2.0 mmol) of p-toluenesulfonic acid are added, and the mixture is stirred under reflux for 16 h. The mixture is then cooled to 0° C., and the solid formed is filtered off and washed once with a little ethanol (batch 1). The mother liquor is concentrated and the residue is triturated with a little ethanol. The solid obtained is filtered off and washed once with ethanol (batch 2). The two solids batches are combined and dried under high vacuum. The solid is then stirred in tert-butyl methyl ether for 30 min, filtered off again and dried under high vacuum.

Workup

  1. temperatureunder reflux for 16 h
  2. customthe solid formed
  3. filtrationis filtered off
  4. washwashed once with a little ethanol (batch 1)
  5. concentrationThe mother liquor is concentrated
  6. customthe residue is triturated with a little ethanol
  7. customThe solid obtained
  8. filtrationis filtered off
  9. washwashed once with ethanol (batch 2)
  10. customdried under high vacuum
  11. stirringThe solid is then stirred in tert-butyl methyl ether for 30 min
  12. filtrationfiltered off again
  13. customdried under high vacuum

Sources & evidence

ORD record
ord-9ec73413d77f491b989bf74bd407b94d
Source dataset
uspto-grants-2013_12
Patent number
US08609698B2

Reaction notes

Loading…