Ammonium Hydroxide → HCID 11234212, compound

HRID 746444Notes

Reaction equation

HRID 746444 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, compoundYield 42%

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 21 mg (42%) of N-(pyrid-4-yl)-4-methoxy-8-acetamido-dibenzo[b,d]furan-1-carboxamide as white solid. mp: 267-268° C.

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

Sources & evidence

ORD record
ord-ca781bd3141644c6892378d065954128
Source dataset
uspto-grants-2008_07
Patent number
US07393846B2

Reaction notes

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