Hydroxylamine → HCID 87505581, compound

HRID 2234020Notes

Reaction equation

HRID 2234020 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)=[CH:19]2)[CH2:14][CH2:13]1)=[O:10].[NH2:25][OH:26]>CCO.CCOC(C)=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[CH2:17][CH2:16][N:15]([N:18]2[CH:22]=[CH:21][C:20](/[CH:23]=[N:25]/[OH:26])=[CH:19]2)[CH2:14][CH2:13]1)=[O:10]

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 86608339HCID 86608339, compound

Product 1

HCID 87505581HCID 87505581, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3,4-dichloro-N-[1-(3-formyl-1H-pyrrol-1-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide (Example 259, 151 mg, 0.41 mmol) and 50% aqueous hydroxylamine (55 μl, 0.83 mmol) in 5 ml EtOH was heated at 80° C. for 30 min. The mixture was diluted with EtOAc and washed with brine. Drying (MgSO4) and removal of solvent gave a solid that was purified by reverse phase HPLC (30-55% gradient CH3CN in water with 0.1% TFA) to give product as a mixture of geometrical isomers.

Workup

  1. washwashed with brine
  2. customDrying
  3. custom(MgSO4) and removal of solvent
  4. customgave a solid
  5. customthat was purified by reverse phase HPLC (30-55% gradient CH3CN in water with 0.1% TFA)
  6. customto give product
  7. additionas a mixture of geometrical isomers

Sources & evidence

ORD record
ord-46fea6d3219b436e8c8d64c1f6806b3c
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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