반응 #166250

반응 방정식

4-(2-fluoro-4-iodophenylamino)-1H-indazole-5-carboxylic acid

O-cyclopropylmethyl-hydroxylamine

EDCI

HOBt

DIPEA

→

title compound

수율 29.2%

4-(2-Fluoro-4-iodo-phenylamino)-1H-indazole-5-carboxylic acid cyclopropylmethoxy-amide

수율 29.2%

용매

ethyl acetate

DMF

반응 조건

후처리

1. 1
   세척washed with saturated aqueous sodium hydrogen carbonate
2. 2
   건조water, dried (Na2SO4)
3. 3
   여과filtered
4. 4
   농축concentrated in vacuo
5. 5
   기타The resultant solid was triturated with a solution of hot methanol/water/NaHCO3
6. 6
   여과the solid filtered off
7. 7
   세척washed with water

실험 절차

To a solution of 4-(2-fluoro-4-iodophenylamino)-1H-indazole-5-carboxylic acid (70 mg, 0.176 mmol) and O-cyclopropylmethyl-hydroxylamine (23 mg, 0.21 mmol) in DMF (3 mL) was added EDCI (40 mg, 0.21 mmol), HOBt (28 mg, 0.21 mmol) and DIPEA (70 μL, 0.42 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate then water, dried (Na2SO4), filtered and concentrated in vacuo. The resultant solid was triturated with a solution of hot methanol/water/NaHCO3, the solid filtered off, washed with water to give the title compound as a pale pink solid (24 mg, 29%). LCMS (Method A): RT=10.42 min, [M+H]+=467. 1H NMR (DMSO-d6, 400 MHz) 13.17 (1 H, s), 7.64 (1 H, dd, J=10.37, 1.95 Hz), 7.48 (1 H, d, J=8.76 Hz), 7.42-7.37 (1 H, m), 7.26 (1 H, d, J=0.95 Hz), 7.01 (1 H, dd, J=8.76, 0.99 Hz), 6.87 (1 H, t, J=8.66 Hz), 3.62 (2 H, d, J=7.13 Hz), 1.08-1.00 (1 H, m), 0.50-0.44 (2 H, m), 0.23-0.17 (2 H, m).

출처