Diisopropylethylamine → HCID 178493641, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-1-(6-fluoro-7-methoxy-1-phenyl-1H-benzoimidazol-2-yl)ethylamine dihydrochloride (0.16 g, 0.44 mmol) in IPA (3 mL) was added 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (139 mg, 0.58 mmol) and DIPEA (229 μL, 1.34 mmol) and the reaction mixture heated at 90° C. for 72 hours. The reaction mixture was concentrated in vacuo and the resultant residue was subjected to flash chromatography (SiO2, eluting with 0-10% methanol in EtOAc) to give a white solid: LCMS (Method C): RT=3.13 min, [M+H]+=488. The solid was dissolved in HCl in methanol (1.25 M, 5 mL) and the reaction mixture stirred at RT for 10 min. The reaction mixture was concentrated in vacuo and the resultant residue subjected to prep. HPLC (C18 phenomonix column, 10-90% MeCN in water 0.1% formic acid, 20 min gradient) to give 338 as a white solid (113 mg, 63%). 1H NMR 400 MHz δ (d6-DMSO): 8.10-8.00 (2H, m), 7.89-7.75 (1H, m), 7.66-7.29 (7H, m), 7.13-7.02 (1H, m), 5.38-5.17 (1H, m), 3.33 (3H, s), 1.48 (3H, d, J=6.8 Hz), LCMS (Method K): RT=3.40 min, [M+H]+=404

Provenance & Evidence