4-Chloroaniline → HCID 59924769, compound

Participants

Reaction Steps

2-[(S)-1-(3-carboxyphenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine (38.1 mg) was dissolved in CH2Cl2 (2 mL), then triethylamine (73 μL) was added followed by 4-chloroaniline (58.9 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (58.0 mg) and 4-dimethylaminopyridine (˜1 mg). The mixture was stirred at room temperature for 45 min then eluted directly on silica gel column (98:2 CH2Cl2:MeOH) then on one 250 μm silica gel plate (1:1 hexanes:acetone) to yield 9.5 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.46 (br s, 1H); 8.39 (d, J=5.5 Hz, 1H); 7.98 (s, 1H); 7.90 (s, 1H); 7.82 (d, J=6.4 Hz, 1H); 7.75 (d, J=7.6 Hz, 1H); 7.65 (d, J=7.6 Hz, 1H); 7.58 (d, J=8.7 Hz, 2H); 7.51 (t, J=7.7 Hz, 1H); 7.33 (m, 3H); 6.80 (d, J=5.5 Hz, 1H); 5.94 (br s, 1H); 5.26 (br s, 1H); 1.67 (d, J=6.9 Hz, 3H). Mass Spectrum (ESI): m/e 469.2 (M+1).

Provenance & Evidence