Reaktion #1031

ord-e90e3b33efd8427982a8d67e8d113a2f

Reaktionsgleichung

CN(C)C=O
DMF
CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)N[C@H]1CCNC[C@H]1OC
cis-N-(3-methoxy-4-piperidinyl)-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide
Fc1ccc(OCCCBr)cc1
3-(4-fluorophenoxy)propyl bromide
CCN(CC)CC
triethylamine
CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)N[C@H]1CCN(CCCOc2ccc(F)cc2)C[C@H]1OC
title compound
Ausbeute 91.8%
CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)N[C@H]1CCN(CCCOc2ccc(F)cc2)C[C@H]1OC
cis-N-[1-[3-(4-Fluorophenoxyl)propyl]-3-methoxy-4-piperidinyl]-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide
Ausbeute 91.8%

Lösungsmittel

Reaktionsbedingungen

Temperatur
50°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturcooled
  2. 2
    WaschenThe obtained mixture was washed with water thrice
  3. 3
    Trocknendried over magnesium sulfate
  4. 4
    SonstigeThe residue was purified by silica gel column chromatography (5% methanol/dichloromethane)

Vorschrift

A mixture comprising 0.10 g of the cis-N-(3-methoxy-4-piperidinyl)-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide, 0.07 g of 3-(4-fluorophenoxy)propyl bromide, 0.20 g of triethylamine and 10 ml of DMF was stirred at 50° C. for 2 hours and cooled. Ethyl acetate was poured into the resulting mixture. The obtained mixture was washed with water thrice, dried over magnesium sulfate, and freed from the solvent. The residue was purified by silica gel column chromatography (5% methanol/dichloromethane) to give 0.13 g of the title compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723472uspto-grants-1998_03