反应详情

温度

23 °C

Acetyl chloride (97 μl, 1.4 mmol) was added dropwise to a solution of N-(4-(2-nitro-2-methylpropoxy)-3-(4-chloro-2-methyl-2H-pyrazol-3-yl)phenyl)-3-(trifluoromethyl)benzamide (68 mg, 0.136 mmol) in MeOH (2.0 mL). Zinc dust (89 mg, 1.4 mmol) was added, and the mixture was stirred at 23° C. After 1 hr, the mixture was filtered and the filtrate was evaporated to dryness. The residue was taken up in ammonium hydroxide (35%), diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried with sodium sulfate, filtered, and evaporated to dryness. The crude product was dissolved in methanol, a solution of acetyl chloride (15 μl) in methanol was added, and the solution was evaporated to dryness. The residue was dissolved in water-acetonitrile 1:1 and lyophilized to afford the product (57 mg, 83%) as the hydrochloride. LCMS ink (%)=469.4 (M+H 37Cl 58.9%), 467.4 (M+H 35Cl 83.7%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.19 (s, 3 H), 1.20 (s, 3 H), 166 (s, 3 H), 3.87 (d, J=9.60 Hz, 1 H), 4.02 (d, J=9.85 Hz, 1 H), 7.31 (d, J=9.09 Hz, 1 H), 7.67 (s, 1 H), 7.72 (d, J=2.53 Hz, 1 H), 7.80 (t, J=7.71 Hz, 1 H), 7.92-8.08 (m, 5 H), 8.27 (d, J=8.08 Hz, 1 H), 8.30 (s, 1 H), 10.58 (s, 1 H).

1. filtrationthe mixture was filtered
2. customthe filtrate was evaporated to dryness
3. additiondiluted with water
4. extractionextracted with ethyl acetate
5. washThe organic layer was washed with brine
6. dry with materialdried with sodium sulfate
7. filtrationfiltered
8. customevaporated to dryness
9. dissolutionThe crude product was dissolved in methanol
10. additiona solution of acetyl chloride (15 μl) in methanol was added
11. customthe solution was evaporated to dryness
12. dissolutionThe residue was dissolved in water-acetonitrile 1:1