1,2-Dichloroethane → (E)-N-[1-(2-hydroxyethyl)-1H-indol-3-ylmethyl]-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide

HRID 1690409

Reaktionsgleichung

Reaktionsgleichung von HRID 1690409
C(Cl)CCl.Cl.[O:6]=[C:7]1[NH:16][C:15]2[N:14]=[CH:13][C:12](/[CH:17]=[CH:18]/[C:19]([OH:21])=O)=[CH:11][C:10]=2[CH2:9][CH2:8]1.[CH2:22]([N:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([CH2:33][NH:34][CH3:35])=[CH:25]1)[CH3:23].C1C=CC2N([OH:45])N=NC=2C=1.O.C(N(C(C)C)CC)(C)C>CN(C=O)C>[OH:45][CH2:23][CH2:22][N:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([CH2:33][N:34]([CH3:35])[C:19](=[O:21])/[CH:18]=[CH:17]/[C:12]2[CH:13]=[N:14][C:15]3[NH:16][C:7](=[O:6])[CH2:8][CH2:9][C:10]=3[CH:11]=2)=[CH:25]1

Komponenten

8

Edukt 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 221391011-ethyl-3-(methylaminomethyl)-1H-indoleHCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid Hydrochloride

Produkt 1

HCID 66780748(E)-N-[1-(2-hydroxyethyl)-1H-indol-3-ylmethyl]-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamideAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

EDC (0.35 g, 1.81 mmole) was added to a solution of (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride salt (0.42 g, 1.65 mmole), 1-ethyl-3-(methylaminomethyl)-1H-indole (0.31 g, 1.65 mmole), HOBt.H2O (0.24 g., 1.81 mmole) and diisopropylethylamine (0.86 mL, 4.95 mmole) in DMF (15 mL) at RT. The reaction was stirred overnight then was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over Na2SO4. Flash chromatography on silica gel (10% EtOH/EtOAc) gave title compound (0.39 g, 61%) as a light yellow solid after drying in vacuo: MS (ES) m/e 389 (M+H)+.

Aufarbeitung

  1. customat RT
  2. concentrationthen was concentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-8a101a096dce43ec8c6bce46846faef5
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153652B2

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