Propan-2-one--water (1/1) → HCID 86722769, compound

HRID 587788Notes

Reaction equation

HRID 587788 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[Cl:7][C:8]1[CH:9]=[C:10]([CH:16]([C:39]([F:42])([F:41])[F:40])/[CH:17]=[CH:18]/[C:19]2[CH:36]=[CH:35][C:22]([C:23]([NH:25][CH2:26][C:27](=[O:34])[NH:28][CH2:29][C:30]([F:33])([F:32])[F:31])=[O:24])=[C:21](SC)[CH:20]=2)[CH:11]=[C:12]([Cl:15])[C:13]=1[F:14].[CH3:43]C(C)=O.O>>[Cl:7][C:8]1[CH:9]=[C:10]([CH:16]([C:39]([F:42])([F:41])[F:40])/[CH:17]=[CH:18]/[C:19]2[CH:20]=[CH:21][C:22]([C:23]([NH:25][CH2:26][C:27](=[O:34])[NH:28][CH2:29][C:30]([F:32])([F:33])[F:31])=[O:24])=[C:35]([S:3]([CH3:43])(=[O:5])=[O:2])[CH:36]=2)[CH:11]=[C:12]([Cl:15])[C:13]=1[F:14]

Participants

4

Reactant 3

HCID 18366337Propan-2-one--water (1/1)HCID 23707502Potassium hydroxy sulfiteHCID 86722770HCID 86722770, compound

Product 1

HCID 86722769HCID 86722769, compound

Procedure

Oxone (320 mg, 0.50 mmol) was added to a stirred solution of (E)-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-2-(methylthio)-N-(2-oxo-2-(2,2,2-trifluoroethylamino)ethyl)benzamide (150 mg, 0.25 mmol) in acetone-water (10 mL, 1:1) at ambient temperature and the reaction mixture was stirred for 18 h. The reaction mixture was then extracted with CH2Cl2. The organic layer was washed with brine and water, dried (Na2SO4), filtered, concentrated and the residue was triturated with pentane-Et2O (1:1) to afford the title compound as an off white solid (85 mg, 56%): 1H NMR (300 MHz, DMSO-d6) δ 9.01 (t, J=6.0, 1H), 8.37 (t, J=6.4 Hz, 1H), 8.08 (s, 1H), 8.01-7.96 (m, 1H), 7.88-7.86 (m, 2H), 7.64 (d, J=7.6 Hz, 1H), 7.05 (dd, J=16.4, 8.8 Hz, 1H), 6.91 (d, J=15.6 Hz, 1H), 4.87-4.80 (m, 1H), 3.98-3.91 (m, 4H), 3.38 (s, 3H); ESIMS m/z 608.85 ([M+H]+); IR (thin film) 337, 416, 721, 164, 768 cm−1.

Workup

  1. extractionThe reaction mixture was then extracted with CH2Cl2
  2. washThe organic layer was washed with brine and water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was triturated with pentane-Et2O (1:1)

Sources & evidence

ORD record
ord-15820abf2b9c4c348f541bc1f8f32745
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

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