HCID 57540720, compound → HCID 57540531, compound

HRID 906231Notes

Reaction equation

HRID 906231 reaction equation
COC1C=CC(C[N:8]2[CH:13]=[CH:12][N:11]=[C:10]([S:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[C:9]2=[O:26])=CC=1>C(O)(C(F)(F)F)=O>[F:25][C:22]([F:23])([F:24])[O:21][C:18]1[CH:17]=[CH:16][C:15]([S:14][C:10]2[C:9](=[O:26])[NH:8][CH:13]=[CH:12][N:11]=2)=[CH:20][CH:19]=1

Participants

3

Reactant 1

HCID 57540720HCID 57540720, compound

Product 1

HCID 57540531HCID 57540531, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1-(4-methoxybenzyl)-3-(4-(trifluoromethoxy)phenylthio)-pyrazin-2(1H)-one (2.76 g, 6.76 mmol) in TFA (25 mL) was stirred at reflux for 2 days. Since LC-MS analysis revealed that 28% SM remained, the reaction was stirred for 7 days. After removal of the TFA under vacuum, the crude product was purified by silica gel chromatography employing a solvent gradient (hexane to 100% EtOAc to elute 3-(4-(trifluoromethoxy)phenylthio)pyrazin-2(1H)-one (1.60 g, 5.27 mmol, 78% yield) as off-white solid. 1H NMR (400 MHz, chloroform-d) δ ppm 7.61 (2H, d, J=9.03 Hz), 7.29 (2H, d, J=7.78 Hz), 7.24 (1H, d, J=4.02 Hz), 7.07 (1H, d).

Workup

  1. temperatureat reflux for 2 days
  2. customAfter removal of the TFA under vacuum
  3. customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-448db9cdb27b4628a2d8845effff6eab
Source dataset
uspto-grants-2011_09
Patent number
US08012984B2

Reaction notes

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