تفاعل #1031

ord-e90e3b33efd8427982a8d67e8d113a2f

معادلة التفاعل

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
المردود 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
المردود 91.8%

المذيبات

ظروف التفاعل

درجة الحرارة
50°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةcooled
  2. 2
    غسيلThe obtained mixture was washed with water thrice
  3. 3
    تجفيفdried over magnesium sulfate
  4. 4
    أخرىThe residue was purified by silica gel column chromatography (5% methanol/dichloromethane)

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05723472uspto-grants-1998_03