Cyanoacetic acid → HCID 71467626, compound

Participants

Reaction Steps

To a stirring solution of 4-chloro-1-(cyclopropylmethyl)-5-[4-(piperazin-1-ylmethyl)phenyl]-1H-benzotriazole (Example 71, 15 mg, 0.039 mmol) in dichloromethane (530 uL) was added cyanoacetic acid (6.7 mg, 0.079 mmol) and (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (31 mg, 0.059 mmol) and diisopropylethylamine (34 uL, 0.20 mmol). After stirring for 2 hours at ambient temperature, the mixture was concentrated in vacuo and the residue was purified by preparative reverse phase HPLC (95:5 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid) to afford the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 8.01 (1H, d, J=8.5 Hz), 7.66 (2H, d, J=7.7 Hz), 7.62 (2H, d, J=7.7 Hz), 7.60 (1H, d, J=8.6 Hz), 4.68 (2H, d, J=7.4 Hz), 4.39 (1H, br s), 2.57-2.46 (10H, m), 1.75-1.72 (2H, m), 1.49-1.38 (1H, m), 0.60-0.56 (2H, m), 0.52-0.49 (2H, m) ppm high resolution mass spectrometry (ES+) m/z 449.1862 [(M+H)+; calculated for C24H26ClN6O: 449.1851].

Provenance & Evidence