1-Pyrrolidineethanamine → HCID 15407405, compound

Participants

Reaction Steps

To a room temperature solution of 2-iodo-11-oxo-11H-pyrido[2,1-b]quinazoline-6-carboxylic acid (2.0 g; 4.97 mmol), 1-(2-aminoethyl)pyrrolidine (1.26 ml; 9.94 mmol), N,N-diisopropylethylamine (4.33 ml; 24,8 mmol), and dichloromethane (50 ml) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (3.3 g; 7.45 mmol) in one portion. After a stirring period of 66 hours, the reaction mixture was diluted with half-saturated sodium bicarbonate (100 ml) and extracted with dichloromethane (3×50 ml). The combined organic phases were washed with brine (70 ml), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by repeated flash chromatography. The first purification on silica gel (250 g; elution with 10% methanol/chloroform) was followed by a second purification (250 g silica gel; elution with 45% methanol/ethyl acetate followed by a gradient elution with 10-20% methanol/chloroform) to provide product as a bright lemon yellow solid: 1.82 g.

Provenance & Evidence