Sodium Bicarbonate → HCID 70978474, compound

Participants

Reaction Steps

Ethyl N-({4-[4-chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]benzyl}carbamoyl)glycinate (Example 83, 30 mg, 0.068 mmol) was dissolved in hydrochloric acid (1.4 mL, 1 N aqueous) and placed into an oil-bath preheated at 100° C. for 1.5 hours. The mixture was cooled to ambient temperature, treated with sodium bicarbonate (aqueous saturated) and extracted with ethyl acetate (3×30 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by preparative reverse phase HPLC (85:15 to 36:64; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid) to afford the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 8.17 (1H, s); 8.00 (1H, d, J=8.5 Hz); 7.58 (1H, d, J=8.6 Hz); 7.49 (2H, d, J=8.2 Hz); 7.41 (2H, d, J=8.2 Hz); 4.67 (2H, d, J=7.2 Hz); 4.62 (2H, s); 4.02 (2H, s); 1.43-1.37 (1H, m); 0.59-0.55 (2H, m); 0.51-0.48 (2H, m) ppm; high resolution mass spectrometry (ES+) m/z 396.1242 [(M+H)+; calculated for C20H19ClN5O2: 396.1222].

Provenance & Evidence