Diisopropylethylamine → HCID 60162685, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-((S)-1-aminoethyl)-5-fluoro-3-phenyl-3H-benzoimidazole-4-carbonitrile dihydrochloride (110 mg, 0.29 mmol) in IPA (3 mL) was added 4-amino-6-chloropyrimidine-5-carbonitrile (45 mg, 0.29 mmol) and DIPEA (148 μL, 0.87 mmol) and the reaction mixture heated at 90° C. for 16 hours. The reaction mixture was concentrated in vacuo and the resultant residue purified by prep HPLC (C18 phenomenex column, 10-90% MeCN in water 0.1% formic acid, 20 min gradient) to give 330 as a white solid (65 mg, 56%). 1H NMR 400 MHz δ (d6-DMSO): 8.08 (1H, dd, J=8.9, 4.9 Hz), 7.78 (1H, s), 7.70 (1H, d, J=7.2 Hz), 7.62-7.56 (1H, m), 7.55-7.43 (4H, m), 7.33 (1H, dd, J=10.4, 9.0 Hz), 7.15 (2H, br s), 5.28 (1H, quin, J=6.9 Hz), 1.48 (3H, d, J=6.9 Hz), LCMS (Method K): RT=3.73 min, [M+H]+=399

Provenance & Evidence