Diisopropylethylamine → HCID 18002310, compound

Participants

Reaction Steps

1-(8-Azabenztriazolyl)-ester of (3Z)-3-({3,5-dimethyl-4-carboxy]1-H-pyrrol-2-yl}methylene)-5-fluoro-1.3-dihydro-2H-indol-2-one (0.5 mmol, 210 mg) [prepared by activating (3Z)-3-(3,3-dimethyl-4-carboxy-1-H-pyrrol-2-ylmethylene)-5-fluoro-1.3-dihydro-2H-indol-2-one (480 mg; 1.6 mmol) with the HATU reagent (570 mg, 1.5 mmol) in the presence of Hunig base (3.0 mmol, 0.525 ml) in DMF (5ml) and isolated in pure form by precipitation with chloroform (5 ml) and drying on high vacuum in 92% yield (579 mg)] was suspended in anhydrous DMA (1.0 ml). A solution of 4-(azetidin-3-yl)-morpholine; (142.5 mg, 1 mmol) in anhydrous DMA (1.0 ml) was added in one portion and the obtained solution was stirred at room temperature for 20 min. The reaction mixture was evaporated at room temperature using an oil pump, the thick residue was diluted with 6 ml of a mixture of methanol plus diethyl amine (20:1; v/v), inoculated mechanically and placed into a refrigerator (+3° C.) for 8 hours. The precipitates were filtered (with a brief wash with an ice-cold methanol) and dried on high vacuum to give the desired product. 71.5% yield (152 mg of an orange solid)

Provenance & Evidence