Hydrochloric Acid → HCID 59186949, compound

HRID 1526087Notes

Reaction equation

HRID 1526087 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-f89a92c9cd034eb897d43182701657c4
Source dataset
uspto-grants-2015_07
Patent number
US09085572B2

Reaction notes

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