Reacción #337616

ord-8ac8f2ed901443ff89b38f366cd51de3

Ecuación de reacción

COC(=O)CNC(=O)c1nc(Cl)c2ccccc2c1OC
[(1-chloro-4-methoxy-isoquinoline-3-carbonyl)-amino]-acetic acid methyl ester
[K+].[OH-]
KOH
COc1c(C(=O)NCC(=O)O)nc(Cl)c2ccccc12
title compound
COc1c(C(=O)NCC(=O)O)nc(Cl)c2ccccc12
[(1-Chloro-4-methoxy-isoquinoline-3-carbonyl)-amino]-acetic acid

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThen the solvent was evaporated in vacuo
  2. 2
    workup.DISSOLUTIONThe residue was dissolved in water (2 ml)
  3. 3
    workup.ADDITIONthe pH of the solution was adjusted to 2-3 by the addition of aqueous 1N HCl
  4. 4
    ExtracciónThe mixture was extracted with EtOAc (4×10 ml)
  5. 5
    Secadophases were dried over MgSO4
  6. 6
    Otroevaporated in vacuo

Procedimiento

A mixture of [(1-chloro-4-methoxy-isoquinoline-3-carbonyl)-amino]-acetic acid methyl ester (21 mg, 0.07 mmol), KOH (23 mg, 0.35 mmol) and EtOH (1 ml) was stirred at ambient temperature for 3 h. Then the solvent was evaporated in vacuo. The residue was dissolved in water (2 ml) and the pH of the solution was adjusted to 2-3 by the addition of aqueous 1N HCl. The mixture was extracted with EtOAc (4×10 ml). The combined org. phases were dried over MgSO4 and evaporated in vacuo to give the title compound as a slightly yellowish solid (18 mg); MS-(+)-ion: M+1=295.0.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07863292B2uspto-grants-2011_01