p-Toluenesulfonic acid → HCID 59280192, compound

HRID 1913205Notes

Reaction equation

HRID 1913205 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].[CH3:17][C:18]([CH3:30])([CH3:29])[CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([NH:27][NH2:28])=[N:25][CH:26]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH3:17][C:18]([CH3:30])([CH3:29])[CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([N:27]2[C:5](=[O:6])[C:4]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)=[CH:3][NH:28]2)=[N:25][CH:26]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 552791605-(2,2-Dimethylpropoxy)-2-hydrazinopyridineHCID 687048643-(Dimethylamino)-2-pyridin-3-yl-acrylic acid ethyl ester

Product 1

HCID 59280192HCID 59280192, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

220 mg (1.0 mmol) of the compound from Example 2A are initially charged in 5 ml of ethanol. 260 mg (purity 75%, 1.0 mmol) of the compound from Example 19A and 38 mg (0.2 mmol) of p-toluenesulfonic acid are added, and the mixture is stirred under reflux for 16 h. The mixture is then allowed to cool to RT, and the solid formed is filtered off, washed with tert-butyl methyl ether and dried under high vacuum. This gives 37 mg of the title compound. The mother liquor is put aside and used for preparing the hydrochloride (see Example 89).

Workup

  1. temperatureunder reflux for 16 h
  2. customthe solid formed
  3. filtrationis filtered off
  4. washwashed with tert-butyl methyl ether
  5. customdried under high vacuum
  6. customused for preparing the hydrochloride (see Example 89)

Sources & evidence

ORD record
ord-dc1f1a445d7643f199b3e88df2c89449
Source dataset
uspto-grants-2013_12
Patent number
US08609698B2

Reaction notes

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