Hydrogen Peroxide → HCID 90311366, compound

HRID 927254Notes

Reaction equation

HRID 927254 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([C:15]([NH:17][CH:18]3[CH2:23][CH2:22][S:21][CH2:20][CH2:19]3)=[O:16])[C:13](=[O:24])[N:12]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=3)[C:11]3[CH2:35][CH2:36][C:37](=[O:38])[C:10]2=3)=[CH:5][CH:4]=1)#[N:2].OO.S([O-])(O)(=O)=[O:42].[K+].O>C(O)C.C[Re](=O)(=O)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[N:14]([C:15]([NH:17][CH:18]3[CH2:19][CH2:20][S:21](=[O:42])[CH2:22][CH2:23]3)=[O:16])[C:13](=[O:24])[N:12]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=3)[C:11]3[CH2:35][CH2:36][C:37](=[O:38])[C:10]2=3)=[CH:7][CH:8]=1)#[N:2]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 516920Potassium bisulfateHCID 903111874-(4-cyanophenyl)-2,5-dioxo-N-(tetrahydro-2H-thiopyran-4-yl)-1-(3-(trifluoromethyl)phenyl)-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-3(2H)-carboxamide

Product 1

HCID 90311366HCID 90311366, compound

Reagents, catalysts & solvents 2

HCID 178477782HCID 178477782, compoundCatalyst2×HCID 702EthanolSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 4-(4-cyanophenyl)-2,5-dioxo-N-(tetrahydro-2H-thiopyran-4-yl)-1-(3-(tri-fluoromethyl)phenyl)-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-3(2H)-carboxamide (example 42.7, 94 mg, 0.18 mmol) in ethanol (1.0 mL) is cooled at −78° C. with an acetone/dry ice bath. Aqueous hydrogen peroxide (36%, 87 μL, 1.0 mmol) is added, and the mixture is stirred at −78° C. for 30 min Methyltrioxorhenium(VII) (1 mg, 4 μmol) is a) added, and the mixture is stirred at −78° C. for 30 min Another portion of methyltrioxo-rhenium(VII) (1 mg, 4 μmol) is added, and the mixture is stirred at −78° C. for 1 h. Aqueous potassium hydrogen sulfate solution (10%, 0.5 mL) and water is (10 mL) is added, and the mixture is filtered. The precipitate is dissolved in N,N-dimethylformamide, and the mixture is purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 40 mg; ESI mass spectrum [M+H]+=557; Retention time HPLC: 0.96 min (Z018_S04).

Workup

  1. additionadded
  2. additionis added
  3. additionis added
  4. filtrationthe mixture is filtered
  5. dissolutionThe precipitate is dissolved in N,N-dimethylformamide
  6. customthe mixture is purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA)
  7. custom0.96 min (Z018_S04)

Sources & evidence

ORD record
ord-2c36e6abfbd54392ae8ada9ae3c14b72
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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