Piperidine → 6-[(1E)-3-Oxo-3-piperidin-1-ylprop-1-en-1-yl]-3,4-dihydro-1,8-naphthyridin-2(1H)-one

HRID 633866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 633866
Cl.[O:2]=[C:3]1[NH:12][C:11]2[N:10]=[CH:9][C:8](/[CH:13]=[CH:14]/[C:15]([OH:17])=O)=[CH:7][C:6]=2[CH2:5][CH2:4]1.[CH:18]1[CH:19]=[CH:20]C2N(O)N=[N:24][C:22]=2[CH:23]=1.CCN(C(C)C)C(C)C.N1CCCCC1.CCN=C=NCCCN(C)C>CN(C=O)C>[O:17]=[C:15]([N:24]1[CH2:20][CH2:19][CH2:18][CH2:23][CH2:22]1)/[CH:14]=[CH:13]/[C:8]1[CH:7]=[C:6]2[C:11](=[N:10][CH:9]=1)[NH:12][C:3](=[O:2])[CH2:4][CH2:5]2

Komponenten

7

Edukt 5

HCID 8082PiperidineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid Hydrochloride

Produkt 1

HCID 529504356-[(1E)-3-Oxo-3-piperidin-1-ylprop-1-en-1-yl]-3,4-dihydro-1,8-naphthyridin-2(1H)-oneAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A 16 mL vial flask was successively charged with (2E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride (50 mg, 0.20 mmol), DMF (4.8 mL), HOBt (32 mg, 0.23 mmol), DIPEA (78 μL, 0.47 mmol), piperidine (23 μL, 0.23 mmol) and EDAC (45 mg, 0.23 mmol). The reaction mixture was stirred at room temperature overnight and concentrated to dryness. The residue was diluted in dichloromethane and washed with water. The organic layer was concentrated to dryness and the residue was purified on preparative TLC (eluent: dichloromethane/MeOH, 95/5) to give the title compound (39 mg, 69%) as a white solid.

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. additionThe residue was diluted in dichloromethane
  3. washwashed with water
  4. concentrationThe organic layer was concentrated to dryness
  5. customthe residue was purified on preparative TLC (eluent: dichloromethane/MeOH, 95/5)

Quellen und Nachweise

ORD-Eintrag
ord-ae5170d58e334c99b6ddd9592339eafb
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321769B2

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