Ethylamine → HCID 59924860, compound

Participants

Reaction Steps

2-[(S)-1-(3-carboxyphenyl)ethylamino]-4-[benzimidazol-1-yl]-pyrimidine (27.4 mg) was dissolved in THF (1 mL), and triethylamine (53 μL) was added. A solution of 2.0M ethylamine in THF (76 μL) was added followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (26.9 mg) and 4-dimethylaminopyridine (˜1 mg). Stirred at room temperature for 2 h then another portion of 2.0M ethylamine in THF (76 μL) was added along with more 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (27.4 mg). 1.5 h later the mixture was concentrated under reduced pressure then purified by silica gel chromatography (98:2 CH2Cl2:MeOH) to yield 18.2 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.48 (br s, 1H); 8.39 (d, J=5.5 Hz, 1H); 7.90 (m, 1H); 7.82 (d, J=7.5 Hz, 1H); 7.64 (m, 1H); 7.58 (d, J=5.8 Hz, 1H); 7.44 (t, J=7.7 Hz, 1H); 7.34 (m, 3H); 6.79 (d, J=5.5 Hz, 1H); 6.11 (br s, 1H); 5.81 (br s, 1H); 5.25 (br s, 1H); 3.49 (m, 2H); 1.65 (d, J=6.9 Hz, 3H); 1.25 (t, J=7.3 Hz, 3H). Mass Spectrum (ESI): m/e 387.1 (M+1).

Provenance & Evidence