Reacción #1509594

ord-8dbd5e9be6624a71b884402429269751

Ecuación de reacción

Cn1nnnc1-c1cc(N)cc(CO)c1
[3-Amino-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-methanol
Cc1cc(N)cc(-c2nnnn2C)c1
title compound
Rendimiento 77.1%
Cc1cc(N)cc(-c2nnnn2C)c1
3-Methyl-5-(1-methyl-1H-tetrazol-5-yl)-phenylamine
Rendimiento 77.1%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrowas hydrogenated on a H-cube apparatus at 30° C.
  2. 2
    OtroAfter reaction completion
  3. 3
    Concentraciónthe mixture was concentrated in vacuum
  4. 4
    ExtracciónThis was extracted with EtOAc
  5. 5
    Otrothe organic layer was separated
  6. 6
    Otrodried
  7. 7
    Concentraciónconcentrated in vacuum
  8. 8
    OtroThe residue was purified by flash chromatography (98:2 DCM:MeOH)

Procedimiento

A solution of [3-Amino-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-methanol (450 mg) in MeOH (20 ml) with a few drops of conc. HCl (aq) was hydrogenated on a H-cube apparatus at 30° C., and 10 bar with a flow rate of 1 mL/min using a Pd/C cartridge. After reaction completion, the mixture was concentrated in vacuum and the residue basified with a dilute K2CO3(aq). This was extracted with EtOAc and the organic layer was separated, dried and concentrated in vacuum. The residue was purified by flash chromatography (98:2 DCM:MeOH) to give the title compound (320 mg).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: USRE045323E1uspto-grants-2015_01