Reaction #1563899

ord-5e17b9c89f1840d683aa9a042fb62ec8

Reaction equation

Nc1nccc2c1nc(Sc1cc3c(cc1Br)OCO3)n2CCCO
Compound 0403-51
Nc1nccc2c1nc(Sc1cc3c(cc1Br)OCO3)n2CCCO
3-(4-Amino-2-(6-bromobenzo[d][1,3]dioxol-5-ylthio)-1H-imidazo[4,5-c]pyridin-1-yl)propan-1-ol
CCN(CC)CC
NEt3
CS(=O)(=O)Cl
MsCl
CS(=O)(=O)OCCCn1c(Sc2cc3c(cc2Br)OCO3)nc2c(N)nccc21
title compound 0404-51
CS(=O)(=O)OCCCn1c(Sc2cc3c(cc2Br)OCO3)nc2c(N)nccc21
3-(4-Amino-2-(6-bromobenzo[d][1,3]dioxol-5-ylthio)-1H-imidazo[4,5-c]pyridin-1-yl)propyl methanesulfonate

Solvents

Conditions

Temperature
40°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ConcentrationThe mixture was concentrated
  2. 2
    Otherpurified by column chromatography on silica gel (CH2Cl2/MeOH=50/1)

Procedure

Compound 0403-51 (264 mg, 0.624 mmol) was dissolved in hot anhydrous dioxane (8.6 mL). The solution was cooled to 40° C. and was treated with NEt3 (189 mg, 1.87 mmol) and MsCl (107 mg, 0.935 mmol) for 20 min. The mixture was concentrated and purified by column chromatography on silica gel (CH2Cl2/MeOH=50/1) to give the title compound 0404-51 as a white solid (143 g, 50%): LCMS: 501 [M+1]+.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09402832B2uspto-grants-2016_08