Dimethyl Sulfide → HCID 57476116, compound

HRID 1994893Notes

Reaction equation

HRID 1994893 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]([CH3:82])([CH2:59][NH:60][C:61]([C:63]1[NH:64][C:65]2[C:70]([CH:71]=1)=[CH:69][CH:68]=[CH:67][C:66]=2[N:72]([CH3:81])[S:73]([C:76]1[S:77][CH:78]=[CH:79][CH:80]=1)(=[O:75])=[O:74])=O)[CH2:45][N:46]1[CH2:51][CH2:50][N:49](C(OC(C)(C)C)=O)[CH2:48][CH2:47]1)C1C=CC=CC=1.CSC.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:81][N:72]([C:66]1[CH:67]=[CH:68][CH:69]=[C:70]2[C:65]=1[NH:64][C:63]([C:61]1[S:43][C:44]([CH3:82])([CH2:45][N:46]3[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]3)[CH2:59][N:60]=1)=[CH:71]2)[S:73]([C:76]1[S:77][CH:78]=[CH:79][CH:80]=1)(=[O:75])=[O:74]

Participants

7

Reactant 5

HCID 1068Dimethyl SulfideHCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 59135589HCID 59135589, compound

Product 1

HCID 57476116HCID 57476116, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of triphenylphosphine oxide (3.09 g) and acetonitrile (20 mL) was slowly added trifluoromethanesulfonic anhydride (0.93 mL) at 0° C., and the mixture was stirred for 10 min. tert-Butyl 4-{2-(benzylthio)-2-methyl-3-[({7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}carbonyl)amino]propyl}piperazine-1-carboxylate (1.55 g) and dimethylsulfide (0.24 mL) were added, and the reaction mixture was stirred at 0° C. for 30 min. Saturated aqueous sodium hydrogencarbonate was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The residue was added to 4N hydrogen chloride-ethyl acetate solution, and the resulting crystals were collected by filtration, and washed with ethyl acetate. The obtained crystals were added to saturated aqueous sodium hydrogencarbonate, and the mixture was stirred for 30 min. The crystals were collected by filtration, washed with water and ethyl acetate, and dried to give the title compound (0.49 g, yield 45%) as colorless crystals. melting point 178-180° C.

Workup

  1. customat 0° C.
  2. additionwere added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. additionThe residue was added to 4N hydrogen chloride-ethyl acetate solution
  8. filtrationthe resulting crystals were collected by filtration
  9. washwashed with ethyl acetate
  10. additionThe obtained crystals were added to saturated aqueous sodium hydrogencarbonate
  11. stirringthe mixture was stirred for 30 min
  12. filtrationThe crystals were collected by filtration
  13. washwashed with water and ethyl acetate
  14. customdried

Sources & evidence

ORD record
ord-1ac010a3961f49aba857c1dfe767664c
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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