Reacción #48781

Ecuación de reacción

DIPEA

3-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]benzoic acid

1-methyl-1-H-pyrazole-3-amine

→

desired compound

Rendimiento 53.4%

3-[4-(Azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

Rendimiento 53.4%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe DMF was removed in vacuo, water
2. 2
   workup.ADDITIONwas added
3. 3
   Extracciónthe mixture extracted with ethyl acetate
4. 4
   Lavadowashed with brine
5. 5
   Secadodried (MgSO4)
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated in vacuo
8. 8
   Otroto give the crude product which
9. 9
   Otrowas chromatographed
10. 10
    Lavadoeluting with 0-100% ethyl acetate in isohexane

Procedimiento

DIPEA (93 mg, 0.72 mmol; 4.0 equivalents) was added to a suspension of 3-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]benzoic acid (70 mg), HATU-(144 mmol; 2.1 equivalents) and 1-methyl-1-H-pyrazole-3-amine (26 mg, 0.27 mmol, 1.5 equivalents) in DMF (2 mL). The resulting mixture was stirred at ambient temperature for 16 hours. The DMF was removed in vacuo, water was added and the mixture extracted with ethyl acetate. The extracts were combined, washed with brine, dried (MgSO4), filtered, and evaporated in vacuo to give the crude product which was chromatographed, eluting with 0-100% ethyl acetate in isohexane, to give desired compound (45 mg).

Fuente