Reaktion #70478

ord-4f731da28ef04aac86202e9425f19f9c

Reaktionsgleichung

CC(O)(COS(C)(=O)=O)c1cnc(N2CCN(c3nnc(Cc4ccccc4)c4ccccc34)CC2)cn1
Methanesulfonic acid 2-[4-(4-benzyl-phthalazin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-5′-yl]-2-hydroxy-propyl ester
OC1CCNCC1
4-hydroxy piperidine
CCN(C(C)C)C(C)C
diisoproylethylamine
CC(O)(CN1CCC(O)CC1)c1cnc(N2CCN(c3nnc(Cc4ccccc4)c4ccccc34)CC2)cn1
title compound
Ausbeute 24.1%
CC(O)(CN1CCC(O)CC1)c1cnc(N2CCN(c3nnc(Cc4ccccc4)c4ccccc34)CC2)cn1
1-{2-[4-(4-Benzyl-phthalazin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-5′-yl]-2-hydroxy-propyl}-piperidin-4-ol
Ausbeute 24.1%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe mixture is heated
  2. 2
    Temperaturto reflux for 16 h
  3. 3
    EinengenConcentrate the crude mixture in vacuo
  4. 4
    SonstigeThe residue is purified by flash chromatography on silica gel (MeOH/CH2Cl2)

Vorschrift

Methanesulfonic acid 2-[4-(4-benzyl-phthalazin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-5′-yl]-2-hydroxy-propyl ester (64 mg, 0.120 mmol) is combined with 4-hydroxy piperidine (61 mg, 0.600 mmol), diisoproylethylamine (63 μL, 0.360 mmol), and acetonitrile (1 mL). The mixture is heated to reflux for 16 h. Concentrate the crude mixture in vacuo. The residue is purified by flash chromatography on silica gel (MeOH/CH2Cl2) to afford the title compound (15.6 mg, 24%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08536168B2uspto-grants-2013_09