Acetonitrile → N-(4-Chloro-3-(5-oxo-1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)benzyl)-2-methylpropane-2-sulfonamide

HRID 509062

Reaction equation

HRID 509062 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][NH:7][S:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])=[CH:4][C:3]=1[C:16]1[NH:20][C:19](=[O:21])[N:18]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[N:17]=1.C(Cl)Cl.C(#N)C.I([O-])(=O)(=O)=[O:39].[Na+]>[Ru](Cl)(Cl)Cl.O>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][NH:7][S:8]([C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:39])=[O:9])=[CH:4][C:3]=1[C:16]1[NH:20][C:19](=[O:21])[N:18]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:31])[F:30])=[CH:24][CH:23]=2)[N:17]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 23667635Sodium periodateHCID 136492443N-(4-Chloro-3-(5-oxo-1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)benzyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 136246115N-(4-Chloro-3-(5-oxo-1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)benzyl)-2-methylpropane-2-sulfonamideYield 25.9%

Reagents, catalysts & solvents 2

HCID 61850Ruthenium trichlorideCatalystHCID 962WaterSolvent

Procedure

To a solution of N-(4-chloro-3-(5-oxo-1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)benzyl)-2-methylpropane-2-sulfinamide (Intermediate-144, 0.075 g, 0.158 mmol) in mixture of DCM:acetonitrile:water (0.2 ml:0.2 mL:0.3 mL), sodium periodate (0.050 g, 0.238 mmol) and ruthenium chloride (0.001 g, 0.003 mmol) were added and the reaction mass was stirred at RT for 4 h. After completion of the reaction the reaction mass was filtered through celite bed and extracted with DCM. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated. The obtained product was purified with column chromatography on neutral alumina eluting with 10% MeOH:DCM to afford 0.020 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 1.30 (s, 9H), 4.31 (d, J=6.0 Hz, 2H), 7.55-7.71 (m, 4H), 7.86 (d, J=8.7 Hz, 2H), 8.19 (d, J=9.0 Hz, 2H), 12.71 (s, 1H). MS (m/z): 489.04 (M+H)+.

Workup

  1. customAfter completion of the reaction the reaction mass
  2. filtrationwas filtered through celite bed
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. customThe obtained product was purified with column chromatography on neutral alumina eluting with 10% MeOH

Sources & evidence

ORD record
ord-0c868207437741ffbd925cf047ff29a7
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Linked notes

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