HCID 58978218, compound → HCID 58978285, compound

HRID 1180109Notes

Reaction equation

HRID 1180109 reaction equation
[CH3:1][NH:2][C:3]([CH2:5][N:6]([CH2:25][C:26](=[O:29])[NH:27][CH3:28])[C:7]([C:9]1[CH:24]=[CH:23][C:12]([C:13]([O:15]CC2C=CC=CC=2)=[O:14])=[CH:11][CH:10]=1)=[O:8])=[O:4]>CO.[Pd]>[CH3:28][NH:27][C:26]([CH2:25][N:6]([CH2:5][C:3](=[O:4])[NH:2][CH3:1])[C:7]([C:9]1[CH:24]=[CH:23][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)=[O:8])=[O:29]

Participants

4

Reactant 1

HCID 58978218HCID 58978218, compound

Product 1

HCID 58978285HCID 58978285, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of Example I (0.73 g, 1.84 mmol) in MeOH (30 mL) was added 10% Pd/C (200 mg). The reaction mixture was then stirred at ambient temperature under 1 atmosphere of H2 for 45 min. The reaction mixture was filtered, the solid washed with EtOH, and the combined organics concentrated in vacuo to yield 4-(bis((methylcarbamoyl)methyl)carbamoyl)benzoic acid (0.52 g, 92% yield). 1H NMR (CDCl3) δ9.16 (s, 1H), 8.05 (d, J=8.4 Hz, 2H), 7.49 (d, J=8.4 Hz, 2H), 4.04 (d, J=6 Hz, 4H), 2.94 (m, 6H); MS (ESI) m/e: 308 (M++1).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid washed with EtOH
  3. concentrationthe combined organics concentrated in vacuo

Sources & evidence

ORD record
ord-d7f92b07e7484732b1013bf6f4ad8389
Source dataset
uspto-grants-2007_10
Patent number
US07279576B2

Reaction notes

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