Triethylamine → 10H-indolo[3,2-b]quinoline-11-carboxylic acid (2-dimethylamino-ethyl)amide

HRID 12262

Reaktionsgleichung

Reaktionsgleichung von HRID 12262
[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]([C:18]([OH:20])=O)=[C:4]1[NH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:5]1=[N:6]2.[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH2:25].C(N(CC)CC)C>O=S(Cl)Cl.C(Cl)Cl>[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH:25][C:18]([C:3]1[C:2]2[C:7](=[CH:8][CH:9]=[CH:10][CH:1]=2)[N:6]=[C:5]2[C:11]3[C:16]([NH:17][C:4]=12)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:20]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 1010675710H-Indolo[3,2-b]quinoline-11-carboxylic acid

Produkt 1

HCID 1147303410H-indolo[3,2-b]quinoline-11-carboxylic acid (2-dimethylamino-ethyl)amideAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

10H-indolo[3,2-b]quinoline-11-carboxylic acid (0.5 g, 1.9 mmol) was dissolved in 20 ml of refluxing SOCl2, After 6 hours a clear solution was obtained, and all volatiles were removed in vacuo. The crude acid chloride was suspended in 10 ml of CH2Cl2. A solution of N,N-dimethylethylendiamine (0.2 mL, 2.26 mmol) and triethylamine (2.2 ml) in 10 ml of CH2Cl2 was added at room temperature, and the mixture was stirred for 14 hours. The organic phase was washed (NaHCO3, brine) and dried (MgSO4). Removal of the solvent and purification by chromatography on alumina (CH2Cl2/MeOH, 90:10) yielded the desired compound (0.38 g, 61%) as a solid. m. p. 175-176° C. 1H-NMR [MeOD, _, ppm]: 8.16 (d, J=7.8 Hz, 1H), 7.92 (m, 2H), 7.35-7.20 (m, 3H), 7.04 (m, 2H), 3.62 (m, 2H, CH2NO), 2.55 (m, 2H, CH2N(CH3)2), 2.29 (s, 6H, N(CH3)j. MS (EI, m/z) 277 (M++1).

Aufarbeitung

  1. customwas obtained
  2. customall volatiles were removed in vacuo
  3. washThe organic phase was washed (NaHCO3, brine)
  4. dry with materialdried (MgSO4)
  5. customRemoval of the solvent and purification by chromatography on alumina (CH2Cl2/MeOH, 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-5ef6c1c4b096459d8233747f623d138d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728000B2

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