Reaktion #328410

Reaktionsgleichung

5-[4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]pyridine-2,3-diamine

ethyl isothiocyanatoformate

dioxane

ethyl isothiocyanatoformate

→

ethyl [1-({3-amino-5-[4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]pyridine-2-yl}amino)ethenyl]carbamate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added each time
2. 2
   EinengenThe mixture was concentrated
3. 3
   Sonstigethe residue purified directly by column chromatography on silica (ethyl acetate)

Vorschrift

A solution of 5-[4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]pyridine-2,3-diamine (188 mg, 0.45 mmol, example 27, step 3) and ethyl isothiocyanatoformate (59 mg, 0.45 mmol) in dioxane (2 mL) was stirred at room temperature for 30 h. After 24 h and 48 h reaction time, additional ethyl isothiocyanatoformate (50 mg, 0.38 mmol) was added each time. The mixture was concentrated and the residue purified directly by column chromatography on silica (ethyl acetate) to give crude ethyl [1-({3-amino-5-[4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]pyridine-2-yl}amino)ethenyl]carbamate (82 mg) which was used in the next step without further purification. MS (EI) for C28H33N7O3S: 548 (MH+).

Quelle