Reaktion #166240

Reaktionsgleichung

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

Ausbeute 68.0%

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

Ausbeute 68.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenbefore being concentrated in vacuo
2. 2
   workup.DISSOLUTIONThe resultant residue was dissolved in ethyl acetate (10 mL)
3. 3
   Waschenwashed with aqueous saturated sodium bicarbonate solution (10 mL)
4. 4
   Extraktionthe aqueous fraction extracted twice with ethyl acetate (2×10 mL)
5. 5
   WaschenThe combined organic extracts were washed with brine (20 mL)
6. 6
   Trocknendried (MgSO4)
7. 7
   Einengenconcentrated in vacuo

Vorschrift

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.

Quelle