Reaktion #1782219

Reaktionsgleichung

2-(((5-Fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-4-carboxylic acid

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

hydroxybenzotriazole

triethylamine

N-(2-aminophenyl)-6-(4-aminobutylamino)nicotinamide

DMF

→

title compound

Ausbeute 73.0%

N-(2-aminophenyl)-6-(4-(2-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)-methyl)-3,5-dimethyl-1H-pyrrole-4-carboxamido)butylamino)nicotinamide

Ausbeute 73.0%

Lösungsmittel

brine

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   FiltrationThe solids were collected by vacuum filtration
3. 3
   Waschenwashed with water
4. 4
   Sonstigedried under vacuum

Vorschrift

2-(((5-Fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-4-carboxylic acid (328 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (384 mg, 2 mmol), hydroxybenzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and N-(2-aminophenyl)-6-(4-aminobutylamino)nicotinamide (314 mg, 1.05 mmol) were added. The mixture was stirred for 20 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (444 mg, 73%) as a red solid. 1H NMR (DMSO-d6)δ1.59 (m, 4H, CH2CH2), 2.32 (s, 3H, pyrrole-CH3), 2.43 (s, 3H, pyrrole-CH3), 3.24 (m, 4H, 2×CH2), 4.85 (s, 2H, benzene-NH2), 6.49 (m, 1H), 6.57 (m, 1H), 6.76 (d, J=8.0 Hz, 1H), 6.85 (m, 1H), 6.93 (m, 1H), 7.12 (d, J=8.0 Hz, 1H), 7.20 (m, 2H), 7.67 (s, 1H), 7.89 (d, J=8.0 Hz, 1H), 8.33 (d, J=8.0 Hz, 1H), 8.63 (s, 2H), 9.35 (s, 1H, benzene-NH), 10.70 (s, 1H, indolinone-NH), 11.82 (s, 1H, pyrrole-NH). LC-MS (m/z) 610 (M+1).

Quelle