Triethylamine → HCID 59924829, compound

Participants

Reaction Conditions

Reaction Steps

2-[(S)-1-(3-carboxyphenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine (35.6 mg) was dissolved in ethanol (3 mL), then p-toluenesulfonic acid hydrate (˜1 mg) was added. The reaction was heated to 80° C. for 20 h after which no reaction progress was observed by thin layer chromatography. To this mixture was then added triethylamine (69 μL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (62 mg) and 4-dimethylaminopyridine (˜1 mg). Stirred at room temperature for 18 h. The mixture was concentrated under reduced pressure. This residue was purified first by silica gel column chromatography (98.5:1.5 CH2Cl2:MeOH) then on a 250 μM silica gel prep plate (1:1 hexanes:acetone) to yield 6.8 mg of the title compound. 1H NMR (500 MHz, CDCl3 partial): δ 8.49 (br s, 1H); 8.45 (d, J=5.4 Hz, 1H); 8.15 (s, 1H); 7.97 (m, 1H); 7.83 (d, J=8.0 Hz, 1H); 7.65 (d, J=7.8 Hz, 1H); 7.46 (t, J=7.7 Hz, 1H); 6.81 (d, J=5.5 Hz, 1H); 5.72 (br s, 1H); 5.27 (br s, 01H); 4.40 (q, J=7.2 Hz, 2H); 1.66 (d, J=7.1 Hz, 3H); 1.41 (t, J=7.2 Hz, 3H). Mass Spectrum (ESI): m/e 388.1 (M+1).

Provenance & Evidence