تفاعل #166248

معادلة التفاعل

O-ethyl hydroxylamine hydrochloride

HOBt

EDCI

DIPEA

DIPEA

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

O-ethyl hydroxylamine hydrochloride

HOBt

EDCI

→

title compound

المردود 37.0%

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

المردود 37.0%

المذيبات

ethyl acetate

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe reaction stirred at room temperature for 18 hours
2. 2
   أخرىAdditional quantities, as at the start of the reaction
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITwas continued for 4 hours
5. 5
   غسيلwashed with saturated aqueous sodium hydrogen carbonate
6. 6
   ترشيحthe solid precipitate in the mixture was filtered off
7. 7
   غسيلwashed with water

الإجراء التجريبي

To a solution of 4-(2-fluoro-4-iodophenylamino)-1H-indazole-5-carboxylic acid (100 mg, 0.252 mmol) in DMF (3 mL) was added O-ethyl hydroxylamine hydrochloride (37 mg, 0.378 mmol), HOBt (37 mg, 0.277 mmol) and EDCI (53 mg, 0.277 mmol). The reaction mixture was stirred at room temperature for 1 hour then DIPEA (91 μl, 0.529 mmol) was added and the reaction stirred at room temperature for 18 hours. Additional quantities, as at the start of the reaction, of O-ethyl hydroxylamine hydrochloride, HOBt, EDCI and DIPEA were added to the reaction and stirring was continued for 4 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate, the solid precipitate in the mixture was filtered off, washed with water to give the title compound (41 mg, 37%). LCMS (Method A): RT=9.65 min, [M+H]+=441. 1H NMR (DMSO-d6, 400 MHz): 13.19 (1 H, s), 11.51 (1 H, s), 9.97 (1 H, s), 7.66 (1 H, dd, J=10.35, 1.95 Hz), 7.46 (1 H, d, J=8.78 Hz), 7.42 (1 H, dd, J=8.47, 1.84 Hz), 7.25 (1 H, s), 7.02 (1 H, d, J=8.76 Hz), 6.91 (1 H, t, J=8.66 Hz), 3.86 (2 H, q, J=7.04 Hz), 1.15 (3 H, t, J=7.03 Hz).

المصدر