Hydrochloric Acid → HCID 59186949, compound

HRID 889307Notes

Reaction equation

HRID 889307 reaction equation
C(O[C:4](=[O:15])[CH:5]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)[C:6](=O)[CH3:7])C.[NH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[NH2:17].CC[O-].[Na+].Cl>C(O)C.O.C(O)(=O)C>[CH3:7][C:6]1[NH:17][N:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[C:4](=[O:15])[C:5]=1[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 786452-HydrazinopyridineHCID 2723922Sodium ethoxideHCID 20228650HCID 20228650, compound

Product 1

HCID 59186949HCID 59186949, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

22 μl glacial acetic acid are added to a solution of 58 mg (0.28 mmol) of the compound from Example 18A and 34 mg (0.31 mmol) 2-hydrazinopyridine in 0.4 ml absolute ethanol and the mixture is stirred overnight at RT. 19 mg sodium ethylate are added and the mixture is subsequently stirred at RT for 30 min and then neutralized with 1 N hydrochloric acid. After addition of water, the mixture is extracted with methylene chloride and the organic phase is dried over magnesium sulfate, filtered and concentrated. The residue is stirred with diisopropyl ether and the solid is filtered off with suction. After drying, 13.5 mg (19% of th.) of the title compound are obtained.

Workup

  1. stirringthe mixture is subsequently stirred at RT for 30 min
  2. extractionthe mixture is extracted with methylene chloride
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. stirringThe residue is stirred with diisopropyl ether
  7. filtrationthe solid is filtered off with suction
  8. customAfter drying

Sources & evidence

ORD record
ord-a8e77abd884940d3a3a83feeb8c48d66
Source dataset
uspto-grants-2012_08
Patent number
US08252817B2

Reaction notes

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