Hydrogen Peroxide → HCID 67499360, compound

HRID 1428356Notes

Reaction equation

HRID 1428356 reaction equation
[Cl:1][C:2]1[C:6]([N:7]([CH2:18][CH3:19])[C:8](=[O:17])[CH2:9][CH:10]([S:15][CH3:16])[C:11]([F:14])([F:13])[F:12])=[CH:5][N:4]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[N:3]=1.FC(F)(F)C([OH:33])C(F)(F)F.OO>>[Cl:1][C:2]1[C:6]([N:7]([CH2:18][CH3:19])[C:8](=[O:17])[CH2:9][CH:10]([S:15]([CH3:16])=[O:33])[C:11]([F:14])([F:13])[F:12])=[CH:5][N:4]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[N:3]=1

Participants

4

Reactant 3

HCID 784Hydrogen PeroxideHCID 135291,1,1,3,3,3-Hexafluoro-2-propanolHCID 67499830HCID 67499830, compound

Product 1

HCID 67499360HCID 67499360, compoundYield 89%

Procedure

To a 20 mL vial was added N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-4,4,4-trifluoro-3-(methylthio)butanamide (82 mg, 0.209 mmol) and hexafluoroisopropanol (1.5 mL). Hydrogen peroxide (0.054 mL, 0.626 mmol, 35% solution in water) was added in one portion and the solution was stirred at room temperature. After 3 hours the reaction was quenched with saturated sodium sulfite solution and extracted with EtOAc (3×20 mL). The combined organic layers were dried over sodium sulfate, concentrated and purified by chromatography (0-10% MeOH/DCM) to give N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-4,4,4-trifluoro-3-(methylsulfinyl)butanamide (76 mg, 0.186 mmol, 89% yield) as white semi-solid: 1H NMR (400 MHz, CDCl3) δ 8.98 (d, J=2.3 Hz, 1H), 8.63 (td, J=4.8, 2.4 Hz, 1H), 8.14-8.01 (m, 2H), 7.46 (ddd, J=8.3, 4.8, 0.7 Hz, 1H), 4.26 (dd, J=17.2, 8.4 Hz, 1H), 3.89-3.61 (m, 2H), 3.01 (dd, J=17.6, 8.2 Hz, 1H), 2.77 (s, 2H), 2.48 (dd, J=17.7, 3.3 Hz, 1H), 1.19 (t, J=7.2 Hz, 3H) (only one isomer shown); ESIMS m/z 409 ([M+H]+); IR (Thin film) 1652 cm−1.

Workup

  1. customAfter 3 hours the reaction was quenched with saturated sodium sulfite solution
  2. extractionextracted with EtOAc (3×20 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by chromatography (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-b9a96ed980fc4666987c8c4e11acbb00
Source dataset
uspto-grants-2015_01
Patent number
US08937083B2

Reaction notes

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