Triethylamine → 6-Chloro-2-[[4-(4-fluorophenyl)-1-piperazinyl]methyl]-imidazo[1,2-a]pyridine

HRID 1416252

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11]Cl)[N:10]=2)[CH:7]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1.C(N(CC)CC)C>C(O)CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:23]3[CH2:22][CH2:21][N:20]([C:17]4[CH:16]=[CH:15][C:14]([F:13])=[CH:19][CH:18]=4)[CH2:25][CH2:24]3)[N:10]=2)[CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 2-(chloromethyl)-6-chloroimidazo[1,2-a]pyridine (Example 4, Step 1; 0.50 g), 1-(4-fluorophenyl)piperazine (Aldrich; 0.471 g), triethylamine (0.277 g), and ethylene glycol (2 mL) is stirred at 80° C. for 1.3 h. After cooling, the mixture is partitioned between dichloromethane and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate and the filtrate is concentrated under reduced pressure. The residue is chromatographed on silica gel using methanol/dichloromethane (2/98) and the appropriate fractions are combined and concentrated. The resulting material is crystallized from dichloromethane/hexane to give 0.66 g of the title compound; mp 129.5-131° C.; MS m/z at 344; IR (mineral oil) 1511, 1236, 1330, 1325, 825 cm-1; 1 H NMR (CDCl3) δ2.74, 3.15, 6.86-6.98, 7.13, 7.52, 7.54, 8.14.

Aufarbeitung

temperatureAfter cooling
customthe mixture is partitioned between dichloromethane and aq. sodium bicarbonate
dry with materialThe organic layers are dried over sodium sulfate
concentrationthe filtrate is concentrated under reduced pressure
customThe residue is chromatographed on silica gel
concentrationconcentrated
customThe resulting material is crystallized from dichloromethane/hexane

Quellen und Nachweise

ORD-Eintrag: ord-7f6fbb05510c4460bc7c44b5446dd088
Quelldatensatz: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05912246

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