Triethylamine → 3-Chloro-4-[4-[(6-chloroimidazo[1,2-a]pyridin-2-yl)methyl]-1-piperazinyl]benzonitrile

HRID 1416270

Reaktionsgleichung

Reaktionsgleichung von HRID 1416270
[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.[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:17]#[N:18].C(N(CC)CC)C>C(N(CC)CC)C.C1COCC1>[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[N:22]1[CH2:27][CH2:26][N:25]([CH2:11][C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]3[CH:8]=2)[CH2:24][CH2:23]1)[C:17]#[N:18]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 48683896-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridineHCID 193671133-Chloro-4-(piperazin-1-yl)benzonitrile

Produkt 1

HCID 193671143-Chloro-4-[4-[(6-chloroimidazo[1,2-a]pyridin-2-yl)methyl]-1-piperazinyl]benzonitrileAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8471TriethylamineKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 6-chloro-2-(chloromethyl)imidazo[1,2-a]pyridine (Example 4, Step 1; 0.140 g), 3-chloro-4-(piperazin-1-yl)benzonitrile (0.155 g), triethylamine (0.078 g), and THF (2.5 mL) is heated at reflux for 5.5 h and then stirred overnight at room temperature. A few drops of triethylamine are then added and the mixture is stirred an additional 4 h at reflux. After cooling, the mixture is concentrated and the residue is partitioned between dichloromethane and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate and concentrated. Chromatography of the residue on silica gel using methanol/dichloromethane (4/96) gives 0.238 g of the title compound. A portion of the material is recrystallized from ethyl acetate/ethyl ether/hexane; mp 137-138° C.; MS m/z 385, 387; IR (mineral oil) 1501, 2225, 1130, 1342, 1490 cm-1. 1H NMR (CDCl3) δ2.77, 3.21, 3.79, 7.03, 7.14, 7.47-7.54, 7.61, 8.14.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 5.5 h
  3. stirringthe mixture is stirred an additional 4 h
  4. temperatureat reflux
  5. temperatureAfter cooling
  6. concentrationthe mixture is concentrated
  7. customthe residue is partitioned between dichloromethane and aq. sodium bicarbonate
  8. dry with materialThe organic layers are dried over sodium sulfate
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-76e8ca55141b496f8f07aeb99139e7e0
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05912246

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