반응 #166253

반응 방정식

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

3-hydroxyazetidine hydrochloride

EDCI

HOBt

DIPEA

→

title compound

수율 49.0%

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

수율 49.0%

용매

ethyl acetate

DMF

반응 조건

후처리

1. 1
   세척washed with saturated aqueous sodium hydrogen carbonate
2. 2
   건조water, dried (Na2SO4)
3. 3
   여과filtered
4. 4
   농축concentrated in vacuo
5. 5
   기타The resultant residue was triturated in cyclohexane

실험 절차

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).

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