Ethyl Acetate → HCID 68423283, compound

HRID 1161518Notes

Reaction equation

HRID 1161518 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[C:15]=2[F:33])[C:11]([NH2:13])=[S:12])=[CH:5][CH:4]=1)#[N:2].F[B-](F)(F)F.[C:39](=O)([O-])O.[Na+].C(OCC)(=O)C>C(#N)C>[CH3:39][S:12][C:11](=[NH:13])[CH:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][Si:23]([CH:27]([CH3:29])[CH3:28])([CH:30]([CH3:32])[CH3:31])[CH:24]([CH3:26])[CH3:25])[C:15]=1[F:33]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 26255Tetrafluoroborate2×HCID 516892Sodium BicarbonateHCID 59517061HCID 59517061, compound

Product 1

HCID 68423283HCID 68423283, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 57.96 g of 2-(4-cyanophenylamino)-2-(2-fluoro-5-methoxy-3-triisopropylsilanyloxyphenyl)thioacetamide in 200 ml of acetonitrile there was added 18.5 g of Me3O+BF4−, and the mixture was stirred at room temperature for 3 hours. After adding 2.1 g of Me3O+BF4− to the reaction mixture, it was further stirred at room temperature for 1 hour. Saturated aqueous sodium hydrogencarbonate was added to the reaction mixture, and extraction was performed with ethyl acetate. After washing the organic layer with saturated brine, it was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off, and the filtrate was concentrated under reduced pressure to give 2-(4-cyanophenylamino)-2-(2-fluoro-5-methoxy-3-triisopropylsilanyloxyphenyl)thioacetimidic acid methyl ester (crude product).

Workup

  1. stirringwas further stirred at room temperature for 1 hour
  2. washAfter washing the organic layer with saturated brine, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. filtrationThe desiccating agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-19c0e22fab3d4e60aa70eee2602a6a0a
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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