تفاعل #1833290

ord-01d2cc3ce5804a8a99308b1c483ed097

معادلة التفاعل

O=C(Nc1cn[nH]c1)c1c(F)cccc1F
2,6-difluoro-N-1H-pyrazol-4-ylbenzamide
O=C(Nc1cnn(Cc2ccccc2COc2ccccc2)c1)c1c(F)cccc1F
intermediate 2
O=C(Nc1cnn(Cc2ccccc2COc2ccccc2)c1)c1c(F)cccc1F
2,6-Difluoro-N-[1-({2-[(phenyloxy)methyl]phenyl}methyl)-1H-pyrazol-4-yl]benzamide
Clc1ccc(CBr)c(OCc2ccccc2)c1
1-(bromomethyl)-4-chloro-2-[(phenylmethyl)oxy]benzene
O=C([O-])[O-].[K+].[K+]
potassium carbonate
O=C(Nc1cnn(Cc2ccc(Cl)cc2OCc2ccccc2)c1)c1c(F)cccc1F
title compound
O=C(Nc1cnn(Cc2ccc(Cl)cc2OCc2ccccc2)c1)c1c(F)cccc1F
N-[1-({4-Chloro-2-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-4-yl]-2,6-difluorobenzamide

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    ترشيحThe suspension was filtered
  2. 2
    غسيلthe residue washed with methanol (1 ml)
  3. 3
    أخرىThe filtrate was purified by MDAP (Method A) on Supelcosil ABZ+Plus column
  4. 4
    أخرىThe solvent was evaporated in vacuo

الإجراء التجريبي

To 2,6-difluoro-N-1H-pyrazol-4-ylbenzamide (for a preparation see intermediate 2, 52 mg, 0.23 mmol) and potassium carbonate (65 mg, 0.47 mmol) was added a solution of 1-(bromomethyl)-4-chloro-2-[(phenylmethyl)oxy]benzene (74 mg, 0.27 mmol) in DMF (1 ml). The reaction was stirred overnight, under nitrogen and at ambient temperature. The suspension was filtered using a hydrophobic frit and the residue washed with methanol (1 ml). The filtrate was purified by MDAP (Method A) on Supelcosil ABZ+Plus column using acetonitrile-water with a formic acid modifier. The solvent was evaporated in vacuo to give the title compound (33 mg) as a white solid; LCMS (System 1): MH+=454, tRET=3.60 min.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09149462B2uspto-grants-2015_10