تفاعل #166253

معادلة التفاعل

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

3-hydroxyazetidine hydrochloride

EDCI

HOBt

DIPEA

→

title compound

المردود 49.0%

[4-(2-Fluoro-4-iodo-phenylamino)-1H-indazol-5-yl]-(3-hydroxy-azetidin-1-yl)-methanone

المردود 49.0%

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 residue was triturated in cyclohexane

الإجراء التجريبي

To a solution of 4-(2-fluoro-4-iodophenylamino)-1H-indazole-5-carboxylic acid (70 mg, 0.176 mmol) and 3-hydroxyazetidine hydrochloride (23 mg, 0.21 mmol) in DMF (1 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 residue was triturated in cyclohexane to give the title compound as a pale tan solid (39 mg, 49%). LCMS (Method A): RT=8.23 min, [M+H]+=453. 1H NMR (DMSO-d6, 400 MHz) 13.17 (1 H, s), 9.55 (1 H, s), 7.63 (1 H, dd, J=10.47, 1.94 Hz), 7.41-7.37 (1 H, m), 7.37 (1 H, s), 7.32 (1 H, d, J=8.69 Hz), 7.05-7.00 (1 H, m), 6.92-6.82 (1 H, m), 5.67 (1 H, d, J=6.13 Hz), 4.44-4.37 (1 H, m), 4.24 (2 H, br, s), 3.83 (2 H, br, s).

المصدر