Ammonium Hydroxide → HCID 11234212, compound

HRID 131607Notes

Reaction equation

HRID 131607 reaction equation
Cl[C:2]1[CH:3]=[N:4][CH:5]=[C:6](Cl)[C:7]=1[NH:8][C:9]([C:11]1[C:19]2[C:18]3[CH:20]=[C:21]([NH:24][C:25](=[O:27])[CH3:26])[CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([O:28][CH3:29])=[CH:13][CH:12]=1)=[O:10].[OH-].[NH4+]>C1COCC1.[Pd]>[N:4]1[CH:3]=[CH:2][C:7]([NH:8][C:9]([C:11]2[C:19]3[C:18]4[CH:20]=[C:21]([NH:24][C:25](=[O:27])[CH3:26])[CH:22]=[CH:23][C:17]=4[O:16][C:15]=3[C:14]([O:28][CH3:29])=[CH:13][CH:12]=2)=[O:10])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 11236119HCID 11236119, compound

Product 1

HCID 11234212HCID 11234212, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(3,5-dichloropyrid-4-yl)-4-methoxy-8-acetamido-dibenzo[b,d]furan-1-carboxamide (60 mg) (Example 4) and 25-28% aqueous ammonium hydroxide (3 ml) in THF (35 ml) was hydrogenated at 50 psi using 10% Pd/C (60 mg) for 24 h at room temperature. The reaction was filtered through celite and the filtrate was concentrated. The residue was dissolved in DCM, washed with water and brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography using 2-10% methanol in DCM as eluent to obtain

Workup

  1. customfor 24 h
  2. customat room temperature
  3. filtrationThe reaction was filtered through celite
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in DCM
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography
  10. customto obtain

Sources & evidence

ORD record
ord-2bbf6fe4ac4b4ed6a8296cc323838237
Source dataset
uspto-grants-2008_06
Patent number
US07384962B2

Reaction notes

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