반응 #166240

반응 방정식

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

O—((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-hydroxylamine

EDCI

HOBt

DIPEA

→

title compound

수율 68.0%

4-(2-Fluoro-4-iodophenylamino)-1H-indazole-5-carboxylic acid ((R)-2,2-dimethyl-[1,3]-dioxolan-4-ylmethoxy)amide

수율 68.0%

용매

DMF

반응 조건

후처리

1. 1
   농축before being concentrated in vacuo
2. 2
   workup.DISSOLUTIONThe resultant residue was dissolved in ethyl acetate (10 mL)
3. 3
   세척washed with aqueous saturated sodium bicarbonate solution (10 mL)
4. 4
   추출the aqueous fraction extracted twice with ethyl acetate (2×10 mL)
5. 5
   세척The combined organic extracts were washed with brine (20 mL)
6. 6
   건조dried (MgSO4)
7. 7
   농축concentrated in vacuo

실험 절차

To a solution of 4-(2-fluoro-4-iodophenylamino)-1H-indazole-5-carboxylic acid (150 mg, 0.38 mmol) and O—((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-hydroxylamine (83 mg, 0.57 mmol) in DMF (4 mL) was added EDCI (80 mg, 0.42 mmol), HOBt (56 mg, 0.42 mmol) and DIPEA (70 μL, 0.42 mmol). The reaction mixture was stirred at room temperature for 3.5 hours before being concentrated in vacuo. The resultant residue was dissolved in ethyl acetate (10 mL), washed with aqueous saturated sodium bicarbonate solution (10 mL) and the aqueous fraction extracted twice with ethyl acetate (2×10 mL). The combined organic extracts were washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si—SPE, gradient 0-10% methanol in DCM) to yield the title compound as a pale yellow solid (135 mg, 68%). LCMS (Method B): RT=3.45 min, [M+H]+=527.

출처