Trifluoroacetic acid → HCID 22391971, compound

HRID 1839170Notes

Reaction equation

HRID 1839170 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[C:16](=[O:17])[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[CH:25]=[N:26][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][CH:29]=4)[CH:19]=3)[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.NC(N)=[O:36].OO.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:1]1([NH:4][C:5]([C:7]2[C:16](=[O:17])[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[CH:25]=[N+:26]([O-:36])[C:27]([S:30]([CH3:33])(=[O:31])=[O:32])=[CH:28][CH:29]=4)[CH:19]=3)[CH:8]=2)=[O:6])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 31294Carbamide Peroxide2×HCID 10183035HCID 10183035, compound

Product 1

HCID 22391971HCID 22391971, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of N-cyclopropyl-1-[3-(6-methylsulfonylpyridin-3-yl)phenyl]-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide from Example 51 in methylene chloride (30 ml/mmol) was added urea-hydrogen peroxide (8 eq) and the resulting mixture was cooled to 0° C. Trifluoroacetic acid (4.7 eq) was added and the mixture was warmed to room temperature as a solution was obtained. After 18 hours, more urea-hydrogen peroxide (2.6 eq) and trifluoroacetic acid (2 eq) were added and stirring was continued for 2 hours. The mixture was quenched with saturated aqueous sodium metabisulfite, diluted with methylene chloride and the organic phase was washed with 1N aqueous HCl, then brine and water, dried and evaporated. The crude product was chromatographed on silica gel eluting with 40% toluene in acetone to afford the title compound as a solid.

Workup

  1. temperaturethe mixture was warmed to room temperature as a solution
  2. customwas obtained
  3. waitwas continued for 2 hours
  4. customThe mixture was quenched with saturated aqueous sodium metabisulfite
  5. additiondiluted with methylene chloride
  6. washthe organic phase was washed with 1N aqueous HCl
  7. dry with materialbrine and water, dried
  8. customevaporated
  9. customThe crude product was chromatographed on silica gel eluting with 40% toluene in acetone

Sources & evidence

ORD record
ord-44ecd1494f694e2680a846ecb02e1e87
Source dataset
uspto-grants-2004_01
Patent number
US06677351B2

Reaction notes

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