Guanidine → HCID 178482792, compound

Participants

Reaction Conditions

Reaction Steps

1-(3-(Dimethylamino)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid, 0.46 g (2.4 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.027 g (0.2 mmol) of 1-hydroxybenzotriazole were added to 0.59 g (10 mmol) of guanidine in 15 cm3 of tetrahydrofuran under an argon atmosphere. After stirring at a temperature in the region of 20° C. for 16 days, the reaction mixture was concentrated to dryness under reduced pressure (2.7 kPa) and the residue was triturated in 20 cm3 of methanol and then filtered. The filtrate was concentrated to dryness under reduced pressure (2.7 kPa) and the residue was purified by flash chromatography on silica gel, elution being carried out with a 100% of dichloromethane to dichloromethane/methanol/triethylamine (50/48/2 by volume) gradient over 90 minutes. After concentrating the fractions comprising the expected product to dryness under reduced pressure (2.7 kPa), the solid obtained was triturated in 20 cm3 of ethanol and filtered off, resulting in 0.004 g of N-[1-(3-(dimethylamino)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]guanidine in the form of a powder melting at 269–271° C. 1H N.M.R. spectrum (300 MHz, (CD3)2SO with addition of a few drops of CD3COOD, δ in ppm): 3.00 (s, 6H), 6.84 (dd, J=8.5 and 2 Hz, 1H), 7.09 (dd, J=8.5 and 2 Hz, 1H), 7.15 (t, J=2 Hz, 1H), 7.39 (t, J=8.5 Hz, 1H), 7.42 (dd, J=8 and 5 Hz, 1H), 8.46 (dd, J=5 and 2 Hz, 1H), 8.55 (dd, J=8 and 2 Hz, 1H), 8.84 (s, 1H).

Provenance & Evidence