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Hydrogen Peroxide → HCID 178458647, compound

HRID 2189837
Notes
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Reaction equation

HRID 2189837 reaction equation
[F:1][C:2]1[C:3]([NH:20][C:21]2[CH:25]=[C:24]([O:26][CH:27]([CH3:29])[CH3:28])[NH:23][N:22]=2)=[N:4][C:5]([NH:10][C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH3:12])=[C:6]([CH:9]=1)[C:7]#[N:8].[OH-:30].[K+].OO>CO>[F:1][C:2]1[C:3]([NH:20][C:21]2[CH:25]=[C:24]([O:26][CH:27]([CH3:29])[CH3:28])[NH:23][N:22]=2)=[N:4][C:5]([NH:10][C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH3:12])=[C:6]([CH:9]=1)[C:7]([NH2:8])=[O:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 178458645HCID 178458645, compound

Product 1

HCID 178458647HCID 178458647, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

(S)-5-Fluoro-2-(1-(4-fluorophenyl)ethylamino)-6-(5-isopropoxy-1H-pyrazol-3-ylamino)nicotinonitrile (Example 16; 0.15 g, 0.38 mmol), was placed in MeOH (7 ml) at 25° C. A 25% aqueous solution (0.4 ml) of KOH (0.11 g, 1.9 mmol) was then added, followed by the addition of 0.1 ml of 30% H2O2. The resulting dark red solution was heated to 65° C. for 1 h, cooled to 25° C., and concentrated. The resulting residue was dissolved in EtOAc (50 ml), washed with water (30 ml), dried, filtered, and concentrated. The resulting solid was purified by column chromatography (DCM-MeOH=25:1) to give the title compound (0.044 g, 28%). 1H NMR (400 MHz, CD3OD) δ 7.75 (d, J=11.7 Hz, 1H), 7.39-7.36 (m, 2H), 7.04-7.00 (m, 2H), 5.37 (s, 1H), 5.11-5.00 (m, 1H), 4.61-4.52 (m, 1H), 1.53 (d, J=7.0 Hz, 3H), 1.31 (m, 6H). MS: Calcd.: 416. Found: [M+H]+ 417.

Workup

  1. temperaturecooled to 25° C.
  2. concentrationconcentrated
  3. dissolutionThe resulting residue was dissolved in EtOAc (50 ml)
  4. washwashed with water (30 ml)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting solid was purified by column chromatography (DCM-MeOH=25:1)

Sources & evidence

ORD record
ord-7bd2feca05f34687a404e1c849782194
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08324252B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes