1,1'-Carbonyldiimidazole → Piperazine,1-(1h-indol-7-ylcarbonyl)-4-(2-pyrimidinyl)-

HRID 1729021

Reaktionsgleichung

Reaktionsgleichung von HRID 1729021
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([OH:12])=O)[CH:3]=[CH:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[N:25]1[CH:30]=[CH:29][CH:28]=[N:27][C:26]=1[N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>CN(C)C=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([N:34]2[CH2:35][CH2:36][N:31]([C:26]3[N:25]=[CH:30][CH:29]=[CH:28][N:27]=3)[CH2:32][CH2:33]2)=[O:12])[CH:3]=[CH:2]1

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 742811H-Indole-7-carboxylic acidHCID 887471-(2-Pyrimidinyl)piperazine

Produkt 1

HCID 19013291Piperazine,1-(1h-indol-7-ylcarbonyl)-4-(2-pyrimidinyl)-Ausbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a chilled solution of indole-7-carboxylic acid (3.22 g; 0.02 mole) in 30ml dimethylformamide was added 1,1'-carbonyldiimidazole (3.24 g; 0.02 mole). This was stirred at ice bath temperature for 40 minutes after whicha solution of 1-(2-pyrimidyl)piperazine (4.1 g; 0.025 moles) was added. This was stirred at ambient temperature for 3 hours and the solvent was concentrated in vacuo. The resulting oil was triturated with water to give5.7 g (93%) of a solid, m.p. 194°-197° C. The solid was recrystallized from methanol/water to give 4.7 g (76%) of 1-(1H-Indol-7-ylcarbonyl)-4-(2-pyrimidinyl)piperazine, m.p. 200°-202° C.

Aufarbeitung

  1. additionwas added
  2. concentrationthe solvent was concentrated in vacuo
  3. customThe resulting oil was triturated with water to give5
  4. customThe solid was recrystallized from methanol/water

Quellen und Nachweise

ORD-Eintrag
ord-8ae7081157794c968f69af760594cf92
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05330986

Verknüpfte Notizen

Wird geladen…