6-Chloro-4-(piperidin-4-ylamino)chromen-2-one → 6-Chloro-4-{1-[5-(4-fluoro-phenyl)-5-oxo-pentyl]-piperidin-4-ylamino}-chromen-2-One

HRID 897199

Reaktionsgleichung

Reaktionsgleichung von HRID 897199
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[C:5]2[NH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:33])[CH2:28][CH2:29][CH2:30][CH2:31]Cl)=[CH:23][CH:22]=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[C:5]2[NH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:31][CH2:30][CH2:29][CH2:28][C:27]([C:24]2[CH:23]=[CH:22][C:21]([F:20])=[CH:26][CH:25]=2)=[O:33])[CH2:16][CH2:15]1

Komponenten

3

Edukt 2

HCID 116376956-Chloro-4-(piperidin-4-ylamino)chromen-2-oneHCID 126497945-Chloro-1-(4-fluorophenyl)-1-oxopentane

Produkt 1

HCID 208178426-Chloro-4-{1-[5-(4-fluoro-phenyl)-5-oxo-pentyl]-piperidin-4-ylamino}-chromen-2-OneAusbeute 34,1 %

Versuchsvorschrift

According to Procedure B above, 6-chloro-4-(piperidin-4-ylamino)-chromen-2-one (0.025 g, 0.05 mmol) and 1-(4-fluorophenyl)-5-chloro-1-oxopentane (0.024 g, 0.11 mmol) were allowed to react to give the title compound (0.0078 g, 27.4%, mono-TFA salt) as a off-white solid. 1H NMR (300 MHz, MeOH) δ ppm 8.05-8.15 (m, 3H), 7.62 (dd, J=3, 9, 1H), 7.35 (d, J=9, 1H), 7.20-7.28 (m, 2H), 5.47 (s, 1H), 3.82-3.92 (m, 1H), 3.67-3.75 (m, 2H), 3.11-3.25 (m, 5H), 2.32-2.43 (m, 2H), 2.15-2.25 (m, 1H), 1.87-2.03 (m, 2H), 1.79-1.87 (m, 4H); MS (ESI+Q1MS) m/z 457 [M]+

Aufarbeitung

  1. customto react

Quellen und Nachweise

ORD-Eintrag
ord-bca0439980534a49a88a690f74d1271d
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921821B2

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