HCID 18956504, compound → HCID 18956546, compound

HRID 1196952Notes

Reaction equation

HRID 1196952 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:30])([CH:16]([C:18]1[CH:19]=[CH:20][C:21]([NH:24]C(OCC)=O)=[N:22][CH:23]=1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1>C(O)(C)C.[OH-].[K+]>[NH2:24][C:21]1[CH:20]=[CH:19][C:18]([CH:16]([CH3:17])[C:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])([OH:30])[CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[CH:23][N:22]=1

Participants

4

Reactant 1

HCID 18956504HCID 18956504, compound

Product 1

HCID 18956546HCID 18956546, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 14797Potassium HydroxideCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of the product of Example 21 (70 mg) in isopropanol (4 ml) containing 50% aqueous potassium hydroxide (4 drops) was heated under reflux for 4 hours and then evaporated. Water was added to the residue and the mixture was extracted several times with ethyl acetate. The combined organic extracts were washed with water and dried (MgSO4). Evaporation of the solvent gave the title compound as an amorphous foam, (49 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. customevaporated
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted several times with ethyl acetate
  6. washThe combined organic extracts were washed with water
  7. dry with materialdried (MgSO4)
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-1a32542180dd43ffa4caa0be00f1df0d
Source dataset
uspto-grants-1992_05
Patent number
US05116844

Reaction notes

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