Reaction #474634

Reaction equation

K2CO3

potassium bis(trimethylsilyl)amide

4-[5-(4-trifluoromethoxy-phenyl)-4H[1,2,4]triazol-3-ylamino]-phenol

4-chloro-2-pyridine-carboxamide

→

TFA

Yield 27.1%

4-{4-[5-(4-trifluoromethoxy-phenyl)-4H-[1,2,4]triazol-3-ylamino]-phenoxy}-pyridine-2-carboxylic acid methylamide trifluoroacetic acid salt

Yield 27.1%

Solvents

MeOH

DMF

Conditions

Workup

1. 1
   OtherThen the vial was capped
2. 2
   Othermicrowaved at 150° C. for 30 min
3. 3
   Filtrationfiltered through 0.22 um syringe
4. 4
   Filtrationfilter
5. 5
   Otherpurified by reverse-phase preparative HPLC in acetonitrile/water system with 0.01% TFA

Procedure

4-[5-(4-trifluoromethoxy-phenyl)-4H[1,2,4]triazol-3-ylamino]-phenol (134.5 mg, 0.4 mmol) was dissolved in 2 mL of anhydrous DMF in a 5 mL microwave vial (Personal Chemistry). Solid potassium bis(trimethylsilyl)amide (120.0 mg, 0.6 mmol) was added and the reaction mixture was stirred with heating at 80° C. for 15 min, then 4-chloro-2-pyridine-carboxamide (68.2 mg, 0.4 mmol) was added, followed by anhydrous K2CO3 (62.0 mg, 0.44 mmol). Then the vial was capped and microwaved at 150° C. for 30 min. Then the reaction mixture was diluted with ca. 1 mL of MeOH, filtered through 0.22 um syringe filter and purified by reverse-phase preparative HPLC in acetonitrile/water system with 0.01% TFA. The product was isolated as a TFA salt (31.7 mg of white solid).

Source