반응 #1031

ord-e90e3b33efd8427982a8d67e8d113a2f

반응 방정식

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
수율 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
수율 91.8%

반응 조건

온도
50°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    온도cooled
  2. 2
    세척The obtained mixture was washed with water thrice
  3. 3
    건조dried over magnesium sulfate
  4. 4
    기타The residue was purified by silica gel column chromatography (5% methanol/dichloromethane)

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05723472uspto-grants-1998_03