تفاعل #166251

معادلة التفاعل

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

O-methyl-hydroxylamine

EDCI

HOBt

DIPEA

→

title compound

المردود 44.0%

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

المردود 44.0%

المذيبات

ethyl acetate

DMF

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with saturated aqueous sodium hydrogen carbonate
2. 2
   تجفيفwater, dried (Na2SO4)
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated in vacuo
5. 5
   أخرىThe resultant solid was triturated with a solution of hot methanol/water/NaHCO3
6. 6
   ترشيحthe solid filtered off
7. 7
   غسيلwashed with water

الإجراء التجريبي

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).

المصدر