Triethylamine → HCID 59924923, compound

Participants

Reaction Steps

2-[(S)-1-(3-carboxyphenyl)ethylamino]-4-[benzimidazol-1-yl]-pyrimidine (0.0376 mmol) and 1-naphthylamine (0.169 mmol) were mixed in CH2Cl2 (2 mL) and then triethylamine (0.187 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (0.172 mmol), and 4-dimethylaminopyridine (˜1 mg) were added in that order. Poor overall solubility was observed so THF (1 mL) was then added to the mixture, which became more homogeneous. The mixture was stirred at room temperature for 22 h then concentrated under reduced pressure. Purified by silica gel chromatography (1-2% MeOH in CH2Cl2) to yield 3.4 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.49 (br s, 1H); 8.41 (d, J=5.5 Hz, 1H); 8.17 (br s, 1H); 8.12 (br s, 1H); 8.02 (br s, 1H); 7.85-7.92 (m, 3H); 7.81 (m, 1H); 7.77 (d, J=8.2 Hz, 1H); 7.69 (d, J=7.5 Hz, 1H); 7.51-7.58 (m, 4H); 7.33 (br s, 2H); 6.82 (d, J=5.5 Hz, 1H); 5.78 (br s, 1H); 5.32 (br s, 1H); 1.71 (d, J=6.9 Hz, 3H). Mass Spectrum (ESI): m/e 485.2 (M+1).

Provenance & Evidence