Oxalyl chloride → (E)-4,4,5,5-tetrafluoro-N-[2-[[2-methyl-6-(2-methylbutoxy)-4-pyridyl]amino]ethyl]-pent-2-enamide

HRID 333076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 333076
[F:1][C:2]([F:11])([CH:8]([F:10])[F:9])/[CH:3]=[CH:4]/[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.[CH3:18][C:19]1[CH:24]=[C:23]([NH:25][CH2:26][CH2:27][NH2:28])[CH:22]=[C:21]([O:29][CH2:30][CH:31]([CH3:34])[CH2:32][CH3:33])[N:20]=1>C(Cl)Cl.CN(C=O)C.C(OCC)(=O)C>[F:11][C:2]([F:1])([CH:8]([F:10])[F:9])/[CH:3]=[CH:4]/[C:5]([NH:28][CH2:27][CH2:26][NH:25][C:23]1[CH:22]=[C:21]([O:29][CH2:30][CH:31]([CH3:34])[CH2:32][CH3:33])[N:20]=[C:19]([CH3:18])[CH:24]=1)=[O:7]

Komponenten

7

Edukt 3

HCID 65578Oxalyl chlorideHCID 66835336N-[2-Methyl-6-(2-methylbutoxy)-4-pyridyl]ethane-1,2-diamineHCID 86691165(E)-4,4,5,5-tetrafluoropent-2-enoic acid

Produkt 1

HCID 86691167(E)-4,4,5,5-tetrafluoro-N-[2-[[2-methyl-6-(2-methylbutoxy)-4-pyridyl]amino]ethyl]-pent-2-enamideAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(E)-4,4,5,5-tetrafluoropent-2-enoic acid (21 mg, 0.12 mmol) was dissolved in DCM (1 ml), oxalyl chloride was added (10 μl, 0.12 mmol) followed by a drop of DMF. The mixture was stirred for 10 minutes at room temperature. N-[2-methyl-6-(2-methylbutoxy)-4-pyridyl]-ethane-1,2-diamine (18 mg, 0.1 mmol) was dissolved in DMF (0.5 ml), the mixtures were combined, TEA (42 μl, 0.3 mmol) was added and the resulting mixture was stirred at room temperature for 1 hour. The mixture was diluted with ethyl acetate, washed with water and saturated sodium bicarbonate solution, dried over magnesium sulfate, the solvent was removed under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 13 mg of a white solid (0.039 mmol, 39%).

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. washwashed with water and saturated sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)

Quellen und Nachweise

ORD-Eintrag
ord-8260f32ef9a2436cb6fe49cb3ede1aa6
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877934B2

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