Pyridine → HCID 22034173, compound

HRID 1792140Notes

Reaction equation

HRID 1792140 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7](=[O:13])[CH:6]=[C:5]2[C:14]([F:17])([F:16])[F:15].[C:18]1([N:24]=[C:25]=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N1C=CC=CC=1>CN(C=O)C>[CH3:12][N:8]1[C:9]2[C:4](=[CH:3][C:2]([NH:1][C:25]([NH:24][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:26])=[CH:11][CH:10]=2)[C:5]([C:14]([F:17])([F:15])[F:16])=[CH:6][C:7]1=[O:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7672Phenyl isocyanateHCID 22034191HCID 22034191, compound

Product 1

HCID 22034173HCID 22034173, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-amino-1-methyl-4-trifluoromethyl-1H-quinolin-2-one (Preparation 1, 48 mg, 200 μmol) in anhydrous DMF (2 mL) was treated with PhNCO (33 μL, 300 μmol) & pyridine (16 μL, 20 μmol). The mixture was stirred for 16 h & then partitioned between EtOAc (30 mL) & H2O (20 mL). The organic layer was washed with H2O (20 mL) & brine (20 mL), before being dried (MgSO4). After filtration, the solution was concentrated & a precipitate formed. This precipitate was collected by filtration & washed with cold EtOAc to give the title compound (58 mg, 80%): δH ((CD3)2SO)=3.60 (s, 3H), 7.00 (t, 1H), 7.10 (s, 1H), 7.30 (t, 2H), 7.45 (d, 2H), 7.65 (d, 1H), 7.75 (dd, 1H), 8.15 (d, 1H), 8.70 (s, 1H), 9.00 (s, 1H); m/z (ES+)=362.2

Workup

  1. custompartitioned between EtOAc (30 mL) & H2O (20 mL)
  2. washThe organic layer was washed with H2O (20 mL) & brine (20 mL)
  3. dry with materialbefore being dried (MgSO4)
  4. filtrationAfter filtration
  5. concentrationthe solution was concentrated
  6. customa precipitate formed
  7. filtrationThis precipitate was collected by filtration
  8. washwashed with cold EtOAc

Sources & evidence

ORD record
ord-b782ccaa18914a638b92100784315792
Source dataset
uspto-grants-2006_07
Patent number
US07074933B2

Reaction notes

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