Reacción #48837

Ecuación de reacción

DIPEA

4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(5-methylpyrazin-2-yl)amino]carbonyl}phenoxy)benzoic acid

HATU

azetidine hydrochloride

→

desired compound

Rendimiento 45.7%

3-[4-(Azetidin-1-ylcarbonyl)phenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(5-methylpyrazin-2-yl)benzamide

Rendimiento 45.7%

Disolventes

Water

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe mixture extracted with ethyl acetate (3×15 mL)
2. 2
   LavadoThe combined organic extracts were washed with brine
3. 3
   Secadodried (MgSO4)
4. 4
   Otroevaporated to a residue which
5. 5
   Otrowas chromatographed on silica
6. 6
   Lavadoeluting with 5% methanol in ethyl acetate

Procedimiento

DIPEA (0.4 mL, 2.08 mmol) was added to a suspension of 4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(5-methylpyrazin-2-yl)amino]carbonyl}phenoxy)benzoic acid (110 mg, 0.26 mmol), HATU (210 mg, 0.55 mmol) and azetidine hydrochloride (49 mg, 0.52 mmol) in DMF (3 mL) and the mixture stirred at RT for 24 hours. Water (30 mL) was added and the mixture extracted with ethyl acetate (3×15 mL). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated to a residue which was chromatographed on silica, eluting with 5% methanol in ethyl acetate, to give the desired compound (55 mg).

Fuente