Dimethyl Sulfide → HCID 59136009, compound

HRID 1960457Notes

Reaction equation

HRID 1960457 reaction equation
C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C([S:43][C:44]1([CH2:54][NH:55][C:56]([C:58]2[NH:59][C:60]3[C:65]([CH:66]=2)=[CH:64][CH:63]=[CH:62][C:61]=3[N:67]([CH3:76])[S:68]([C:71]2[S:72][CH:73]=[CH:74][CH:75]=2)(=[O:70])=[O:69])=O)[CH2:53][CH2:52][C:47]2([O:51][CH2:50][CH2:49][O:48]2)[CH2:46][CH2:45]1)C1C=CC=CC=1.CSC.C(=O)([O-])O.[Na+]>C(#N)C>[S:43]1[C:44]2([CH2:53][CH2:52][C:47]3([O:51][CH2:50][CH2:49][O:48]3)[CH2:46][CH2:45]2)[CH2:54][N:55]=[C:56]1[C:58]1[NH:59][C:60]2[C:65]([CH:66]=1)=[CH:64][CH:63]=[CH:62][C:61]=2[N:67]([CH3:76])[S:68]([C:71]1[S:72][CH:73]=[CH:74][CH:75]=1)(=[O:70])=[O:69]

Participants

7

Reactant 5

HCID 1068Dimethyl SulfideHCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 59135872HCID 59135872, compound

Product 1

HCID 59136009HCID 59136009, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of triphenylphosphine oxide (1.98 g) in acetonitrile (30 mL) was slowly added trifluoromethanesulfonic anhydride (0.60 mL) at 0° C., and the mixture was stirred for 10 min. N-{[8-(Benzylthio)-1,4-dioxaspiro[4.5]dec-8-yl]methyl}-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (1.45 g) and dimethylsulfide (0.52 mL) were added, and the reaction mixture was stirred at 0° C. for 30 min. Saturated aqueous sodium hydrogencarbonate was added, and the precipitated solid was collected by filtration, and washed with water. The obtained solid was washed with ethyl acetate, and dried to give the title compound (0.75 g, yield 63%) as colorless crystals. melting point 224-225° C.

Workup

  1. customat 0° C.
  2. stirringthe reaction mixture was stirred at 0° C. for 30 min
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with water
  5. washThe obtained solid was washed with ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-5e3a7015c3024b898e798ae89907466d
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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