Pyridine → HCID 21940001, compound

HRID 1242888Notes

Reaction equation

HRID 1242888 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].N1C=CC=CC=1.[CH3:12][N:13]([CH2:15][CH:16]1[CH2:25][C:24]2[C:19](=[CH:20][C:21]([NH:26][C:27]([C:29]3[CH:34]=[CH:33][C:32]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:31][CH:30]=3)=[O:28])=[CH:22][CH:23]=2)[NH:18][CH2:17]1)[CH3:14].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH3:14][N:13]([CH2:15][CH:16]1[CH2:25][C:24]2[C:19](=[CH:20][C:21]([NH:26][C:27]([C:29]3[CH:30]=[CH:31][C:32]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:33][CH:34]=3)=[O:28])=[CH:22][CH:23]=2)[N:18]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:17]1)[CH3:12]

Participants

6

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chloride2×HCID 21940004HCID 21940004, compound

Product 1

HCID 21940001HCID 21940001, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonyl chloride (0.02 ml) was added to pyridine solution (1 ml) of N-[3-[(N,N-dimethylamino)methyl]-1,2,3,4-tetrahydro-7-quinolinyl]-4-biphenylcarboxamide (80 mg) under ice-cooling, which was stirred at room temperature for 1 hour. Further, methanesulfonyl chloride (0.02 ml) was added to the reaction mixture under ice-cooling, which was stirred at room temperature for 12 hours. 10% aqueous potassium carbonate solution was added to the reaction mixture, 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 (64 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringwhich was stirred at room temperature for 12 hours
  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-0073541e555f446b86e4e975edcdd3e8
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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