Reacción #805897

Ecuación de reacción

compound 83c

5-(8-morpholino-2-((quinolin-2-yloxy)methyl)imidazo[1,2-b]pyridazin-3-yl)picolinonitrile

sodium azide

triethylamine hydrochloride

→

title compound 33

2-((3-(6-(1H-tetrazol-5-yl)pyridin-3-yl)-8-morpholinoimidazo[1,2-b]pyridazin-2-yl)methoxy)quinoline

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched by the addition of 10 mL of water
2. 2
   FiltraciónThe solids were collected by filtration
3. 3
   OtroThe crude product was purified by flash column chromatography on silica gel (methanol/DCM, 1:200-1:10)

Procedimiento

A solution of compound 83c (200 mg, 0.430 mmol), sodium azide (85 mg, 1.31 mmol) and triethylamine hydrochloride (300 mg, 2.17 mmol) in N,N-dimethylformamide (3 mL) was stirred for 2 h at 110° C. The reaction was quenched by the addition of 10 mL of water. The solids were collected by filtration. The crude product was purified by flash column chromatography on silica gel (methanol/DCM, 1:200-1:10) to afford title compound 33 as a yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 9.13 (s, 1H), 8.52-8.50 (m, 1H), 8.38-8.36 (m, 1H), 8.26-8.22 (m, 2H), 7.88 (d, J=7.6 Hz, 1H), 7.64-7.59 (m, 2H), 7.43-7.39 (m, 1H), 7.04 (d, J=8.8 Hz, 1H), 6.49-6.48 (m, 1H), 5.68 (s, 2H), 4.05-3.98 (m, 4H), 3.85-3.75 (m, 4H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C26H22N10O2: 507.2 (M+H). Found: 507.1.

Fuente