反应详情

To a solution of 2-amino-5-(2-benzyloxy-2H-pyrazol-3-yl)-4-trifluoromethyl-benzoic acid methyl ester (263 mg, 0.672 mmol) in DCM (15 mL) were added successively Et3N (0.37 mL, 2.69 mmol) and then (CCl3O)2CO (163 mg, 0.53 mmol). The resulting mixture was stirred at r.t. for 2.5 h. The solvent was removed in vacuo and the residue was solubilised in THF. CH3SO2NHNH2 (98 mg, 0.87 mmol) was added. After stirring the mixture at r.t. for 2.5 h, it was treated with aq NaOH (1N, 0.87 mL) for 30 min. The solvent was removed in vacuo and water was added. The pH was adjusted to 3-4 by addition of 1N aq HCl. The aqueous phase was extracted with AcOEt (2×). The organic phases were combined, washed with brine, dried (Na2SO4) and concentrated in vacuo to afford a yellow syrup. The crude product was purified by flash chromatography (silica gel, DCM/MeOH (100:0 to 90:10)) to provide the title compound as an off-white solid (100 mg, 30%). ES-MS: m/z 496.3 [M+H]+, rt 5.81 min.

1. customThe solvent was removed in vacuo
2. stirringAfter stirring the mixture at r.t. for 2.5 h
3. customThe solvent was removed in vacuo and water
4. additionwas added
5. additionThe pH was adjusted to 3-4 by addition of 1N aq HCl
6. extractionThe aqueous phase was extracted with AcOEt (2×)
7. washwashed with brine
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated in vacuo
10. customto afford a yellow syrup
11. customThe crude product was purified by flash chromatography (silica gel, DCM/MeOH (100:0 to 90:10))