Acetic Acid → HCID 21063028, compound

HRID 1242886Notes

Reaction equation

HRID 1242886 reaction equation
[C:1](O)(=[O:3])C.[CH3:5][N:6]([CH2:8][CH:9]1[CH2:18][C:17]2[C:12](=[CH:13][C:14]([NH:19][C:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:24][CH:23]=3)=[O:21])=[CH:15][CH:16]=2)[NH:11][CH2:10]1)[CH3:7].C(=O)([O-])[O-].[K+].[K+]>C(O)=O>[CH3:7][N:6]([CH2:8][CH:9]1[CH2:18][C:17]2[C:12](=[CH:13][C:14]([NH:19][C:20]([C:22]3[CH:23]=[CH:24][C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:26][CH:27]=3)=[O:21])=[CH:15][CH:16]=2)[N:11]([CH:1]=[O:3])[CH2:10]1)[CH3:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 21940004HCID 21940004, compound

Product 1

HCID 21063028HCID 21063028, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
55 °C

Procedure

Anhydrous acetic acid (0.1 ml) was added to formic acid (1 ml), which was stirred at 55° C. for 2 hours. N-[3-[(N,N-dimethylamino)methyl]-1,2,3,4-tetrahydo-7-quinolinyl]-4-biphenylylcarboxamide (80 mg) was added to the reaction mixture under ice-cooling, which was stirred at room temperature for 72 hours. 10% aqueous potassium carbonate solution was added to the reaction mixture to make the mixture alkaline, and extraction was conducted using ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was recrystallized using THF-IPE to give the titled compound (80 mg).

Workup

  1. temperaturecooling
  2. stirringwhich was stirred at room temperature for 72 hours
  3. extractionthe mixture alkaline, and extraction
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was recrystallized

Sources & evidence

ORD record
ord-a74a646d666d435bb63d23877dcb60d4
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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