Imidazole → 9-[2-(1-Imidazolyl)ethyl]-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole

HRID 482322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 482322
CS(O[CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[C:17]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[N:18][C:19]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:20][C:9]1=2)(=O)=O.[NH:31]1[CH:35]=[CH:34][N:33]=[CH:32]1>C1(C)C(C)=CC=CC=1>[N:31]1([CH2:6][CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3[C:17]([N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[N:18][C:19]([N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[N:20][C:9]2=3)[CH:35]=[CH:34][N:33]=[CH:32]1

Komponenten

4

Edukt 2

HCID 795ImidazoleHCID 537324089-(2-Methanesulfonyloxyethyl)-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole

Produkt 1

HCID 190640889-[2-(1-Imidazolyl)ethyl]-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A mixture of 9-(2-methanesulfonyloxyethyl)-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole (IX, EXAMPLE4, 0.64 g), imidazole (1.02 g) and xylene (15 mL) is heated at reflux for 3 hr. The xylene is then removed under reduced pressure, and the residue is partitioned between methylene chloride and aqueous sodium bicarbonate. The organic phase is washed with saline, dried over sodium sulfate and concentrated. Chromatography (silica gel, 4% methanol/methylene chloride) gives the title compound, mp=181°-183°; NMR (CDCl3) 7.88, 7.40, 7.14-7.09, 7.01-6.97, 6.82, 4.56-4.54, 4.44-4.42, 3.92, 3.63 and 1.99 δ.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 3 hr
  3. customThe xylene is then removed under reduced pressure
  4. customthe residue is partitioned between methylene chloride and aqueous sodium bicarbonate
  5. washThe organic phase is washed with saline
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-86a5c43cf7724ebf9cfa85c4e4cc492c
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05795986

Notizen zur Reaktion

Wird geladen…