Trifluoroacetic acid → HCID 59397840, compound

HRID 39758Notes

Reaction equation

HRID 39758 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[CH:8][C:9](=[O:29])[N:10]2[CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([NH:21]C(=O)OC(C)(C)C)[CH2:17][CH2:16]2)=[C:5]([C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)[CH:4]=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[NH2:21][CH:18]1[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][N:10]2[C:11]3[C:6](=[C:5]([C:30]4[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=4)[CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[N:7]=[CH:8][C:9]2=[O:29])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59398408HCID 59398408, compound

Product 1

HCID 59397840HCID 59397840, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 2 mL of a chloroform solution containing 280 mg of tert-butyl (1-(2-(7-methoxy-5-(pyridin-4-yl)-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 0.84 mL of trifluoroacetic acid was added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, chloroform and water were added thereto, the resultant solution was adjusted to pH about 12 with a 2 mol/L aqueous sodium hydroxide solution, and the organic layer was separated. The organic layer was washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 230 mg of a yellow oily substance, 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-5-(pyridin-4-yl)quinoxalin-2(1H)-one.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure, chloroform and water
  3. additionwere added
  4. customthe organic layer was separated
  5. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9ed6de9bd9584749bd9d96e119c22ebd
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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