Sodium percarbonate → (S)-4-(3,5-dichlorophenyl)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)quinoline-2-carboxamide

HRID 2422548Notes

Reaction equation

HRID 2422548 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:18]3[C:13](=[CH:14][C:15]([CH2:19][N:20]4[CH:24]=[C:23]([C@:25]([OH:32])([C:28]([F:31])([F:30])[F:29])[CH2:26][CH3:27])[N:22]=[N:21]4)=[CH:16][CH:17]=3)[N:12]=[C:11]([C:33]#[N:34])[CH:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C([O-])([O-])=[O:36].C([O-])([O-])=O.OO.OO.OO.[Na+].[Na+].[Na+].[Na+]>CC(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:18]3[C:13](=[CH:14][C:15]([CH2:19][N:20]4[CH:24]=[C:23]([C@:25]([OH:32])([C:28]([F:31])([F:29])[F:30])[CH2:26][CH3:27])[N:22]=[N:21]4)=[CH:16][CH:17]=3)[N:12]=[C:11]([C:33]([NH2:34])=[O:36])[CH:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 159762Sodium percarbonateHCID 66790617(S)-4-(3,5-dichlorophenyl)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)quinoline-2-carbonitrile

Product 1

HCID 66790081(S)-4-(3,5-dichlorophenyl)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)quinoline-2-carboxamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a solution of (S)-4-(3,5-dichlorophenyl)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)quinoline-2-carbonitrile (30 mg, 0.059 mmol) in acetone (1.5 mL) and water (1 mL) was added sodium percarbonate (28 mg, 0.18 mmol). After 1.5 h at 50° C., the reaction was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduce pressure. Purification on silica gel (eluting with acetone/dichloromethane, 2:8) gave the title compound. MS (+ESI): 524 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification on silica gel (eluting with acetone/dichloromethane, 2:8)

Sources & evidence

ORD record
ord-7d77c0fbfda54cbaa18c96189040a6fd
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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