반응 #166248

반응 방정식

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

수율 37.0%

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

수율 37.0%

용매

ethyl acetate

DMF

반응 조건

후처리

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

실험 절차

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).

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