反応 #166251

反応方程式

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

O-methyl-hydroxylamine

EDCI

HOBt

DIPEA

→

title compound

収率 44.0%

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

収率 44.0%

溶媒

ethyl acetate

DMF

反応条件

後処理

1. 1
   洗浄washed with saturated aqueous sodium hydrogen carbonate
2. 2
   乾燥water, dried (Na2SO4)
3. 3
   ろ過filtered
4. 4
   濃縮concentrated in vacuo
5. 5
   その他The resultant solid was triturated with a solution of hot methanol/water/NaHCO3
6. 6
   ろ過the solid filtered off
7. 7
   洗浄washed with water

実験手順

To a solution of 4-(2-fluoro-4-iodophenylamino)-1H-indazole-5-carboxylic acid (70 mg, 0.176 mmol) and O-methyl-hydroxylamine (19 mg, 0.21 mmol) in DMF (2 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 (33 mg, 44%). LCMS (Method A): RT=9.09 min, [M+H]+=427. 1H NMR (DMSO-d6, 400 MHz) 13.20 (1 H, s), 11.62 (1 H, s), 9.99 (1 H, s), 7.66 (1 H, dd, J=10.33, 1.94 Hz), 7.46-7.40 (2 H, m), 7.23 (1 H, s), 7.01 (1 H, d, J=8.78 Hz), 6.92 (1 H, t, J=8.66 Hz), 3.64 (3 H, s).

出典