Potassium peroxymonosulphate → HCID 71539176, compound

HRID 707452Notes

Reaction equation

HRID 707452 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5](SC)=[C:6]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][C@@H:15]3[CH3:20])[N:11]=[C:10]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][CH3:31])=[O:29])=[CH:23][CH:22]=3)[N:9]=2)[CH:7]=1.[S:34]([O-:39])(O[O-])(=O)=[O:35].[K+].[K+].OOS([O-])=O.[K+].[CH2:48]1COCC1.CO.O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:34]([CH3:48])(=[O:39])=[O:35])=[C:6]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][C@@H:15]3[CH3:20])[N:11]=[C:10]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][CH3:31])=[O:29])=[CH:23][CH:22]=3)[N:9]=2)[CH:7]=1

Participants

5

Reactant 4

HCID 10313463Potassium peroxymonosulphateHCID 21892291Methanol tetrahydrofuran waterHCID 23707502Potassium hydroxy sulfiteHCID 89463485HCID 89463485, compound

Product 1

HCID 71539176HCID 71539176, compoundYield 46%

Procedure

(S)-1-(4-(4-(5-fluoro-2-(methylthio)phenyl)-6-(3-methylmorpholino)-1,3,5-triazin-2-yl)phenyl)-3-methylurea (258 mg, 0.55 mmol) was stirred with Potassium peroxymonosulfate (Oxone) (1.01 g, 1.65 mmol) in THF:MeOH:H2O (5:3:2)(10 ml) for 1 hour at 0° C. Reaction allowed to reach room temperature and stirred overnight with more oxone (1.01 g, 1.65 mmol). The mixture is quenched with saturated sodium thiosulfate solution (10 ml). Diluted with DCM (50 mL) and washed with brine (50 mL). The organic layer was passed through a hydrophobic frit and concentrated in vacuo. The resulting solid was purified by prep HPLC at to afford the title compound as a yellow solid. (127 mg, Yield 46%)

Workup

  1. customReaction
  2. customto reach room temperature
  3. customThe mixture is quenched with saturated sodium thiosulfate solution (10 ml)
  4. additionDiluted with DCM (50 mL)
  5. washwashed with brine (50 mL)
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid was purified by prep HPLC at

Sources & evidence

ORD record
ord-3c6a151c9bfd46ecba9494472c22961c
Source dataset
uspto-grants-2015_11
Patent number
US09175011B2

Reaction notes

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