Hydrochloric Acid → HCID 58277435, compound

HRID 1949255Notes

Reaction equation

HRID 1949255 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Cl:20])[CH:14]=3)=[CH:11][C:10]([C:21]([O:23]CC)=[O:22])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Li+].O.Cl>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Cl:20])[CH:14]=3)=[CH:11][C:10]([C:21]([OH:23])=[O:22])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 58277324HCID 58277324, compound

Product 1

HCID 58277435HCID 58277435, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

688 mg of the compound of Example 51A with 76% purity (1.23 mmol) are provided in 29 ml of tetrahydrofuran and, at room temperature, 389 mg (16.2 mmol) of lithium hydroxide and 10 ml of water are added. The mixture is stirred at room temperature for 5 h, a 1N aqueous hydrogen chloride solution is subsequently added until the pH is acidic, and the mixture is extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated. The residue is stirred in a little cyclohexane and the precipitate is collected by suction filtration. 413 mg (83% of theory) of the title compound are obtained.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. stirringThe residue is stirred in a little cyclohexane
  6. filtrationthe precipitate is collected by suction filtration

Sources & evidence

ORD record
ord-a8a8655ac1594722bace3b68c215e1ca
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

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