Reacción #640527

ord-dde274e722b0409d87706d81630193ab

Ecuación de reacción

N#CCCNc1nonc1-c1nc2ccccc2[nH]1
4-(1H-benzimidazol-2-yl)-furazan-3-yl-N-(2-cyanoethyl)-amine
N#CCCNc1nonc1-c1nc2ccccc2[nH]1
4-(1H-Benzimidazol-2-yl)-furazan-3-yl-N-(2-cyanoethyl)-amine
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
C1CCOC1
THF
C1CCOC1
THF
OCCCNc1nonc1-c1nc2ccccc2[nH]1
title compound
OCCCNc1nonc1-c1nc2ccccc2[nH]1
4-(1H-Benzimidazol-2-yl)-furazan-3-yl-N-(3-hydroxypropyl)-amine

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrois quenched by careful addition of aqueous saturated solution of sodium sulphate
  2. 2
    FiltraciónThe suspension is filtered
  3. 3
    Otrothe filtrate evaporated to dryness
  4. 4
    OtroCrystallization
  5. 5
    workup.ADDITIONby addition of hexane

Procedimiento

A solution of 4-(1H-benzimidazol-2-yl)-furazan-3-yl-N-(2-cyanoethyl)-amine (0.272 g, 0.947 mmol, Example 6a) in THF (5 ml) is added dropwise at 0° C. to an efficiently stirred suspension of LiAlH4 (0.054 g, 1.42 mmol) in THF (5 ml). After stirring for 16 hours at room temperature the mixture is quenched by careful addition of aqueous saturated solution of sodium sulphate. The suspension is filtered and the filtrate evaporated to dryness. Crystallization by addition of hexane yields the title compound in pure form. 1H-NMR (400 MHz, d6-DMSO): 13.6 (s, 1H); 7.66 (m, 2H); 7.31 (m, 2H); 6.92 (t, 1H); 4.61 (m, 1H); 3.51 (m, 2H); 3.39 (m, 2H); 1.81 (m, 2H).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: USRE042890E1uspto-grants-2011_11