Diisopropylethylamine → HCID 68412236, Verbindung

HRID 659119

Reaktionsgleichung

Reaktionsgleichung von HRID 659119
[C:1]1([C:7]2[O:11][C:10]([C:12]([OH:14])=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][O:16][C:17](=[O:28])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[C:22]([NH2:27])[CH:21]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH3:15][O:16][C:17](=[O:28])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[C:22]([NH:27][C:12]([C:10]2[O:11][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][CH:9]=2)=[O:14])[CH:21]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 7362555-Phenylfuran-2-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 684148563-(3-Amino-4-fluoro-phenyl)-acrylic acid methyl ester

Produkt 1

HCID 68412236HCID 68412236, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-phenyl-2-furoic acid (36) (18 mg, 0.15 mmol) was coupled to aniline (43) (30 mg, 0.15 mmol) using Method B, except that DIPEA (40 mg, 0.31 mmol) and DMF (2 mL) were used and the reaction was stirred at ambient temperature for 2.5 hours, then at 40° C. for 24 hours. Further TBTU (1 eq) and acid (1 eq) were added and the reaction heated at 60° C. for a further 6 hours to give the crude title compound after work-up. The residue was purified using column chromatography eluting with 20% EtOAc in heptane to give the title compound. Yield: 18 mg, 32%; LC-MS tr 1.55 min; HPLC Purity: 83%; MS (ES+) m/z 366 (M+H)

Aufarbeitung

  1. waitat 40° C. for 24 hours
  2. temperaturethe reaction heated at 60° C. for a further 6 hours
  3. customto give the crude title compound after work-up
  4. customThe residue was purified
  5. washeluting with 20% EtOAc in heptane

Quellen und Nachweise

ORD-Eintrag
ord-7b9f03991b584eac8f90f41084015ef1
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080567B2

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