5-Fluoroindole-2-carboxylic acid → 5-fluoro-2-{[4-(2-pyridinyl)-1-piperazinyl]carbonyl}-1H-indole

HRID 1768350

Reaktionsgleichung

Reaktionsgleichung von HRID 1768350
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.CCN=C=NCCCN(C)C.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:34]1[CH2:35][CH2:36][N:31]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][N:25]=3)[CH2:32][CH2:33]1)=[O:13])=[CH:5]2

Komponenten

5

Edukt 3

HCID 18205-Fluoroindole-2-carboxylic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 944591-(2-Pyridyl)piperazine

Produkt 1

HCID 220659825-fluoro-2-{[4-(2-pyridinyl)-1-piperazinyl]carbonyl}-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

5-Fluoro-1H-indole-2-carboxylic acid (4.0 g) and EDCI (4.29 g) were combined in dichloromethane (90 mL) and treated with 1-(2-pyridinyl)piperazine (3.64 g). After stirring at 25° C. for 24 hours, the mixture was washed with 150 mL of water and filtered. The filter cake was washed in succession with 300 mL of water, 250 mL of dichloromethane and 20 mL of ethyl acetate to provide the title compound. 1H NMR (d6-DMSO, 300 MHz) δ 3.61 (m, 4H), 3.85 (m, 4H), 6.67 (dd, 1H, J=7.5,4.8 Hz), 6.85 (m, 2H), 7.06 (m, 1H), 7.40 (m, 2H), 7.65 (m, 1H), 8.04 (dd, 1H, J=4.5,1.8 Hz), 11.72 (bs, 1H). MS (DCI/NH3) m/z 325 (M+H)+.

Aufarbeitung

  1. washthe mixture was washed with 150 mL of water
  2. filtrationfiltered
  3. washThe filter cake was washed in succession with 300 mL of water, 250 mL of dichloromethane and 20 mL of ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0bb1c775ac38489b876892e306f82b36
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07235661B2

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