1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 136377294, compound

Participants

Reaction Steps

5-Oxo-5,6-dihydroimidazo[1,2-c]pyrimidine-2-carboxylic acid (0.323 mmol, 0.058 g), HBTU (0.027 mmol, 10.21 mg), DIPEA (0.323 mmol, 0.042 g) and EDCI (0.323 mmol, 0.062 g) were suspended in DMF (2 ml) and the resulting mixture was stirred at RT for 10 min. (S)-4-(1-(2-Aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (0.269 mmol, 0.1 g) dissolved in DMF (2 ml) was added and the resulting mixture was stirred for 17 h at RT. At this point more starting materials were added so that the amount of every starting material was raised by half of the original amount. The amount of (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile was not changed. The reaction was continued for another 22 h after which the temperature was raised to 80° C. for 4.5 h. The reaction mixture was diluted with EtOAc and washed with 1M Na2CO3, brine and water. The organic phase was dried, filtered and evaporated. The crude product was purified by preparative HPLC. 0.006 g of the title compound was obtained. 1H-NMR (400 MHz, MeOH-d4): δ 1.25 (d, 3H), 4.30-4.37 (m, 1H), 4.42-4.49 (m, 1H), 4.54-4.65 (m, 1H), 6.61 (dd, 1H), 6.70 (d, 1H), 7.18 (d, 1H), 7.63 (d, 1H), 7.75-7.82 (m, 2H), 8.26 (s, 1H).

Provenance & Evidence