Triphenylphosphine Oxide → N-methyl-N-[2-methyl-5-(1-thia-3,8-diazaspiro[4.5]deca-2-en-2-yl)-4H-thieno[3,2-b]pyrrol-3-yl]thiophene-2-sulfonamide

HRID 453589Notes

Reaction equation

HRID 453589 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([CH2:50][NH:51][C:52]([C:54]2[NH:58][C:57]3[C:59]([N:63]([CH3:72])[S:64]([C:67]4[S:68][CH:69]=[CH:70][CH:71]=4)(=[O:66])=[O:65])=[C:60]([CH3:62])[S:61][C:56]=3[CH:55]=2)=O)[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1)C1C=CC=CC=1>ClCCl>[CH3:72][N:63]([C:59]1[C:57]2[NH:58][C:54]([C:52]3[S:43][C:44]4([CH2:49][CH2:48][NH:47][CH2:46][CH2:45]4)[CH2:50][N:51]=3)=[CH:55][C:56]=2[S:61][C:60]=1[CH3:62])[S:64]([C:67]1[S:68][CH:69]=[CH:70][CH:71]=1)(=[O:66])=[O:65]

Participants

5

Reactant 3

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 59411373N-{[4-(benzylthio)piperidin-4-yl]methyl}-2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxamide

Product 1

HCID 59411372N-methyl-N-[2-methyl-5-(1-thia-3,8-diazaspiro[4.5]deca-2-en-2-yl)-4H-thieno[3,2-b]pyrrol-3-yl]thiophene-2-sulfonamideYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of triphenylphosphine oxide (1.5 g) in dichloromethane (20 mL) was slowly added trifluoromethanesulfonic anhydride (0.45 mL) at 0° C., and the mixture was stirred for 10 min. N-{[4-(Benzylthio)piperidin-4-yl]methyl}-2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxamide (1.03 g) was added, and the mixture was stirred at room temperature for 3 hr and concentrated. Saturated aqueous sodium hydrogen carbonate 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 subjected to silica gel column chromatography to give N-methyl-N-[2-methyl-5-(1-thia-3,8-diazaspiro[4.5]deca-2-en-2-yl)-4H-thieno[3,2-b]pyrrol-3-yl]thiophene-2-sulfonamide (240 mg, yield 29%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). melting point 196° C.

Workup

  1. customat 0° C.
  2. stirringthe mixture was stirred at room temperature for 3 hr
  3. concentrationconcentrated
  4. additionSaturated aqueous sodium hydrogen carbonate was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-905cbec386f04e588048e911dadddcdf
Source dataset
uspto-grants-2013_07
Patent number
US08492405B2

Reaction notes

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