Potassium Permanganate → HCID 68579982, compound

HRID 2234021Notes

Reaction equation

HRID 2234021 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([N:18]2[CH:22]=[CH:21][C:20]([CH:23]=[O:24])=[CH:19]2)[CH2:14][CH2:13]1)=[O:10].[O-:25][Mn](=O)(=O)=O.[K+]>CC(C)=O.O>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:13][CH2:14][N:15]([N:18]2[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19]2)[CH2:16][CH2:17]1)=[O:10]

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 86608339HCID 86608339, compound

Product 1

HCID 68579982HCID 68579982, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

Solutions of 3,4-dichloro-N-[1-(3-formyl-1H-pyrrol-1-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide (Example 259, 90 mg, 0.24 mmol) in 10 ml acetone and KMNO4 (39 mg, 0.24 mmol) in 3 ml water were combined and stirred at ambient temperature overnight. Due to incomplete conversion, solutions of KMnO4 (15 and 20 mg) in 3 ml water were added at 5 hour intervals. The mixture was quenched with aqueous NaHSO3 and partitioned between EtOAc and water. The EtOAc was separated and washed with brine. Drying (MgSO4) and removal of solvent gave product as a white solid.

Workup

  1. customThe mixture was quenched with aqueous NaHSO3
  2. custompartitioned between EtOAc and water
  3. customThe EtOAc was separated
  4. washwashed with brine
  5. customDrying
  6. custom(MgSO4) and removal of solvent
  7. customgave product as a white solid

Sources & evidence

ORD record
ord-e9d7d8b77cc74b4e806876443a2a92e0
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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