HCID 18956504, compound → HCID 18956546, compound

HRID 1591340Notes

Reaction equation

HRID 1591340 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-957ef716b58c440eb07e4f49fac42fcd
Source dataset
uspto-grants-1993_04
Patent number
US05206364

Reaction notes

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