Hydrogen Peroxide → HCID 86682248, compound

HRID 1428377Notes

Reaction equation

HRID 1428377 reaction equation
[Cl:1][C:2]1[C:6]([N:7]([CH2:14][C:15]#[CH:16])[C:8](=[O:13])[CH:9]([S:11][CH3:12])[CH3:10])=[CH:5][N:4]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[N:3]=1.[OH:23]O>>[Cl:1][C:2]1[C:6]([N:7]([CH2:14][C:15]#[CH:16])[C:8](=[O:13])[CH:9]([S:11]([CH3:12])=[O:23])[CH3:10])=[CH:5][N:4]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[N:3]=1

Participants

3

Reactant 2

HCID 784Hydrogen PeroxideHCID 86682247HCID 86682247, compound

Product 1

HCID 86682248HCID 86682248, compoundYield 78%

Procedure

To a solution of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-2-(methylthio)-N-(prop-2-yn-1-yl)propanamide (0.1 g, 0.30 mmol) in hexafluoroisoproanol (2.0 ml) was added hydrogen peroxide (35 wt %, 0.08 ml, 0.90 mmol) and the reaction mixture was stirred vigorously at ambient temperature. The reaction was complete after 1 h. The reaction was quenched with saturated sodium sulfite solution and the organic layer was extracted with EtOAc (3×20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified using silica gel chromatography (0-20% methanol (MeOH)/DCM) to afford the title compound as an off-white foam (82 mg, 0.21 mmol, 78%): 1H NMR (400 MHz, CDCl3) δ 8.98 (s, 1H), 8.65 (d, J=4.6 Hz, 1H), 8.23 (s, 1H), 8.11-7.97 (m, 1H), 7.51-7.41 (m, 1H), 4.88 (br s, 1H), 4.14 (br s, 1H), 2.64 (s, 1.2H), 2.55 (s, 1.8H), 2.33-2.27 (m, 1H), 1.47 (d, J=6.8 Hz, 3H), 1.42 (br s, 1H); 13C NMR (101 MHz, CDCl3) δ 168.11, 148.95, 148.78, 140.45, 140.33, 140.20, 135.56, 126.54, 124.10, 121.68, 121.58, 121.48, 77.69, 73.49, 38.60; ESIMS m/z 351 ([M+H]+).

Workup

  1. customThe reaction was quenched with saturated sodium sulfite solution
  2. extractionthe organic layer was extracted with EtOAc (3×20 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-82b75316f74d4b17bb4f339b3ba90149
Source dataset
uspto-grants-2015_01
Patent number
US08937083B2

Reaction notes

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