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Triphenylphosphine Oxide → N-{5-[5-(dimethoxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]-2-methyl-4H-thieno[3,2-b]pyrrol-3-yl}-N-methylthiophene-2-sulfonamide

HRID 453593
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 453593
[CH3:1][C:2]1[S:9][C:8]2[CH:7]=[C:6]([C:10](O)=O)[NH:5][C:4]=2[C:3]=1[N:13]([CH3:22])[S:14]([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)(=[O:16])=[O:15].C([S:30][CH:31]([CH:34]([O:37][CH3:38])[O:35][CH3:36])[CH2:32][NH2:33])C1C=CC=CC=1.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(=O)([O-])O.[Na+].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>ClCCl.C(#N)C.O1CCCC1>[CH3:36][O:35][CH:34]([O:37][CH3:38])[CH:31]1[S:30][C:10]([C:6]2[NH:5][C:4]3[C:3]([N:13]([CH3:22])[S:14]([C:17]4[S:18][CH:19]=[CH:20][CH:21]=4)(=[O:16])=[O:15])=[C:2]([CH3:1])[S:9][C:8]=3[CH:7]=2)=[N:33][CH2:32]1
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Komponenten

11

Edukt 7

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574759902-(Benzylthio)-3,3-dimethoxypropan-1-amine
HCID 59411385
2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxylic acid

Produkt 1

HCID 59411383N-{5-[5-(dimethoxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]-2-methyl-4H-thieno[3,2-b]pyrrol-3-yl}-N-methylthiophene-2-sulfonamideAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxylic acid (1.0 g), 2-(benzylthio)-3,3-dimethoxypropan-1-amine (720 mg), 1H-1,2,3-benzotriazol-1-ol (450 mg), tetrahydrofuran (10 mL) and acetonitrile (10 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (570 mg), and the mixture was stirred at room temperature for 30 min. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give a colorless oil. To a solution of triphenylphosphine oxide (252 mg) in dichloromethane (3 mL) was slowly added trifluoromethanesulfonic anhydride (76 μL) at 0° C., the mixture was stirred for 10 min, and the colorless oil was added. 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-{5-[5-(dimethoxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]-2-methyl-4H-thieno[3,2-b]pyrrol-3-yl}-N-methylthiophene-2-sulfonamide (245 mg, yield 27%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). melting point 185° C.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give a colorless oil
  6. customat 0° C.
  7. stirringthe mixture was stirred for 10 min
  8. additionthe colorless oil was added
  9. stirringThe mixture was stirred at room temperature for 3 hr
  10. concentrationconcentrated
  11. additionSaturated aqueous sodium hydrogen carbonate was added
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe ethyl acetate layer was washed with saturated brine
  14. dry with materialdried (MgSO4)
  15. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b409b92be6404c508a6d71fe736acee5
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08492405B2

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