Hydrochloric Acid → HCID 178495867, compound

HRID 402730Notes

Reaction equation

HRID 402730 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[O:15][C:14]([NH:16][CH2:17][CH2:18][O:19][CH3:20])=[C:13](C(OC)=O)[C:12]2=[O:25])=[CH:2]1.[OH-].[K+].Cl>C(O)C>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[C:12](=[O:25])[CH:13]=[C:14]([NH:16][CH2:17][CH2:18][O:19][CH3:20])[O:15]2)=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 178495868HCID 178495868, compound

Product 1

HCID 178495867HCID 178495867, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound (0.070 g, 0.20 mmol) of Example 98 in ethanol (2.0 mL), 50% potassium hydroxide solution (1.0 mL, 0.018 mol) was added at ambient temperature. The mixture was refluxed for 1 h. Cooled to ambient temperature, 1M hydrochloric acid was added to adjust pH to acidic, and then the solvent was removed under reduced pressure. To this residue, ethanol (2.0 mL) and water (2.0 mL) were added then refluxed for 1 h. Cooled to ambient temperature, the solvent was removed under reduced pressure, and the residue was purified by preparative HPLC to afford the titled compound as solid (0.0060 g, y. 12%).

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. customwas removed under reduced pressure
  3. additionTo this residue, ethanol (2.0 mL) and water (2.0 mL) were added
  4. temperaturethen refluxed for 1 h
  5. temperatureCooled to ambient temperature
  6. customthe solvent was removed under reduced pressure
  7. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-89010d1d32be472995f72876b6771ea8
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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