HCID 86679264, compound → HCID 86679265, compound

HRID 1519694Notes

Reaction equation

HRID 1519694 reaction equation
C([O:8][NH:9][C:10](=[O:33])[C:11]([N:17]([C:19]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)=[O:20])[CH3:18])([CH3:16])[C:12]([NH:14][CH3:15])=[O:13])C1C=CC=CC=1.[H][H]>[Pd].CO>[C:24]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:23]=[CH:22][C:21]([C:19]([N:17]([CH3:18])[C:11]([CH3:16])([C:12]([NH:14][CH3:15])=[O:13])[C:10]([NH:9][OH:8])=[O:33])=[O:20])=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 86679264HCID 86679264, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86679265HCID 86679265, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd—C (36 mg) was added to a methanol (3.0 mL) solution of N-(benzyloxy)-2-[(biphenyl-4-ylcarbonyl)(methyl)amino]-N′,2-dimethylpropanediamide (0.10 g) as obtained in Example 12-(3), and the mixture was stirred in a hydrogen atmosphere for 4 hours at room temperature. The reaction mixture was filtered through Celite, and the solvent was distilled off. The residue was purified by preparative silica gel thin-layer chromatography (chloroform/methanol=14/1) to obtain 2-[(biphenyl-4-ylcarbonyl)(methyl)amino]-N-hydroxy-N′,2-dimethylpropanediamide (Compound 324, yellow solid) (38 mg, 48%).

Workup

  1. customas obtained in Example 12-(3)
  2. filtrationThe reaction mixture was filtered through Celite
  3. distillationthe solvent was distilled off
  4. customThe residue was purified by preparative silica gel thin-layer chromatography (chloroform/methanol=14/1)

Sources & evidence

ORD record
ord-7903ecc4ac344f8091b3686cedc5a118
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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