Thiophene-3-carboxylic acid → N-(3-Iodo-4-methylphenyl)thiophene-3-carboxamide

HRID 1988876Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1988876
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[CH:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[I:43][CH2:44][C:45]1[CH:46]=C(C=C[CH:51]=1)N.CC[N:54]([CH:58]([CH3:60])[CH3:59])C(C)C>CN(C=O)C>[I:43][C:44]1[CH:60]=[C:58]([NH:54][C:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)=[O:8])[CH:59]=[CH:51][C:45]=1[CH3:46]

Komponenten

7

Edukt 5

HCID 6918Thiophene-3-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 686784243-Iodomethylaniline

Produkt 1

HCID 21914512N-(3-Iodo-4-methylphenyl)thiophene-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Thiophene-3-carboxylic acid (2.75 g) and HATU (8.15 g) in DMF (25 ml) were stirred at room temp for 15 min. HOBT (2.9 g), 3-iodomethylaniline (5.0 g) and DIPEA (11.2 ml, 64.35 mmol) were added and the reaction was stirred at room temp for 16 h. The solvent was evaporated under vacuum and the residue was partitioned between ethyl acetate (100 ml) and aqueous sodium carbonate (10%, 100 ml). The aqueous layer was extracted with ethyl acetate (50 ml) and the combined organic phases washed with hydrochloric acid (2N, 75 ml), water (75 ml) and brine (75 ml). The organic phase was dried (magnesium sulphate) and absorbed onto silica. The silica was applied to a silica column and eluted with cyclohexane/ethyl acetate (4:1). The solvent was evaporated from the product fractions under vacuum to the tide compound.

Aufarbeitung

  1. customThe solvent was evaporated under vacuum
  2. customthe residue was partitioned between ethyl acetate (100 ml) and aqueous sodium carbonate (10%, 100 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate (50 ml)
  4. washthe combined organic phases washed with hydrochloric acid (2N, 75 ml), water (75 ml) and brine (75 ml)
  5. dry with materialThe organic phase was dried (magnesium sulphate)
  6. customabsorbed onto silica
  7. washeluted with cyclohexane/ethyl acetate (4:1)
  8. customThe solvent was evaporated from the product fractions under vacuum to the tide compound

Quellen und Nachweise

ORD-Eintrag
ord-8e6667ea2ec8496f899d3ac51963f8b0
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07642276B2

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