Pyridine → HCID 10407518, compound

HRID 1743285Notes

Reaction equation

HRID 1743285 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12](Cl)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[C:5]([C:16]([F:19])([F:18])[F:17])=[CH:4][C:3]1=[O:20].[C:21]1([NH2:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N1C=CC=CC=1>CN(C=O)C.CCOC(C)=O>[C:21]1([NH:27][S:12]([C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[N:2]([CH3:1])[C:3](=[O:20])[CH:4]=[C:5]3[C:16]([F:19])([F:18])[F:17])(=[O:14])=[O:13])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 6115AnilineHCID 22055308HCID 22055308, compound

Product 1

HCID 10407518HCID 10407518, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-methyl-2-oxo-4-trifluoromethyl-1,2-dihydroquinoline-6-sulfonyl chloride (Preparation 1, 65 mg, 200 μmol) in anhydrous DMF (1.5 mL) was contacted with PhNH2 (19 μL, 210 μmol), employing pyridine (17 μL, 220 μmol) as base), before being stirred overnight under N2. The reaction mixture was diluted with EtOAc (70 mL), before being washed with H2O (30 mL), 1 M HCl (30 mL), H2O (30 mL), saturated aqueous NaHCO3 (30 mL), H2O (30 mL), & brine (30 mL). After drying (MgSO4), the organic phase was filtered & concentrated to give a residue that was recrystallised from EtOAc-PE to furnish the title compound (39 mg, 50%): δH ((CD3)2SO)=3.60 (s, 3H), 7.00 (s, 1H), 7.10 (d, 2H), 7.15–7.20 (m, 3H), 7.80 (d, 1H), 8.00–8.05 (m, 2H); m/z (ES+)=383.1 [M+H]+.

Workup

  1. washbefore being washed with H2O (30 mL), 1 M HCl (30 mL), H2O (30 mL), saturated aqueous NaHCO3 (30 mL), H2O (30 mL), & brine (30 mL)
  2. dry with materialAfter drying (MgSO4)
  3. filtrationthe organic phase was filtered
  4. concentrationconcentrated
  5. customto give a residue that
  6. customwas recrystallised from EtOAc-PE

Sources & evidence

ORD record
ord-2145bc99577b465795c3842e265a4246
Source dataset
uspto-grants-2006_03
Patent number
US07009052B2

Reaction notes

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