Phenylacetyl chloride → HCID 18332602, compound

Participants

Reaction Steps

To a solution of 2-[1-(piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine (EXAMPLE 18) (28.2 mg, 0.087 mmol) in CH2Cl2 (1.0 mL) was added triethylamine (18 μL, 0.131 mmol) followed by phenylacetyl chloride (17 μL, 0.131 mmol) at 0° C. The reaction mixture was gradually warmed to room temperature and stirred for 5 h. The reaction mixture was diluted with EtOAc (10 mL), washed with saturated aqueous NaHCO3 followed by brine, and dried over Na2SO4. The crude product was purified by preparative thin layer chromatography (1:1 acetone:hexane) to yield 19.8 mg of the title compound. Presence of rotamers in Partial 1H NMR (500 MHz, CDCl3): δ 8.6 (s, 1H); 8.36 (d, J=5.3 Hz, 1H); 8.14 (m, 1H); 7.86 (m, 1H); 7.4-7.22 (aromatic H's, 7H); 6.78 (m, 1H); 4.67 (m, 1H); 3.73 (s, 2H); 1.31 (d, J=6.8 Hz, 1.5H); 1.11 (d, J=6.8 Hz, 1.5H). Mass spectrum 441.4 (ESI, M+1).

Provenance & Evidence