Reaktion #1509686

ord-507c6be4bec44b1d94a65881f79c3143

Reaktionsgleichung

CC(C)n1cnc2c(Cl)nc(-c3csc4ccccc34)nc21
2-(benzo[b]thiophen-3-yl)-6-chloro-9-isopropyl-9H-purine
NCCc1c[nH]c2ccc(O)cc12
serotonin
CC(C)n1cnc2c(NCCc3c[nH]c4ccc(O)cc34)nc(-c3csc4ccccc34)nc21
title compound
CC(C)n1cnc2c(NCCc3c[nH]c4ccc(O)cc34)nc(-c3csc4ccccc34)nc21
3-(2-(2-(benzo[b]thiophen-3-yl)-9-isopropyl-9H-purin-6-ylamino)ethyl)-1H-indol-5-ol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    EinengenThe reaction mixture was concentrated
  2. 2
    workup.ADDITIONaqueous sodium bicarbonate solution was added
  3. 3
    ExtraktionThe mixture was extracted with ethyl acetate
  4. 4
    Trocknendried over sodium sulfate
  5. 5
    Einengenconcentrated
  6. 6
    SonstigeThe residue was purified by silica gel chromatography (0 to 5% MeOH in DCM eluant)

Vorschrift

Following the procedure of Example 15e, 2-(benzo[b]thiophen-3-yl)-6-chloro-9-isopropyl-9H-purine (b) (80 mg, 0.243 mmol) was reacted with serotonin. The reaction mixture was concentrated, then aqueous sodium bicarbonate solution was added. The mixture was extracted with ethyl acetate. The organic fractions were combined, dried over sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (0 to 5% MeOH in DCM eluant) to afford the title compound as an off-white solid. MS m/z 469.2 (M+1).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08927281B2uspto-grants-2015_01