Diisopropylethylamine → HCID 68158145, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of [2-((S)-1-aminoethyl)-5-fluoro-3-phenyl-3H-benzoimidazol-4-yl]-morpholin-4-ylmethanone dihydrochloride (300 mg, 0.69 mmol) in IPA (5 mL) was added 4-amino-6-chloropyrimidine-5-carbonitrile (108 mg, 0.69 mmol) and DIPEA (353 mL, 2.07 mmol) and the reaction mixture heated at 90° C. for 16 h. The reaction mixture was concentrated in vacuo and the resultant residue subjected to flash chromatography (SiO2, eluting with 0-4% methanol in EtOAc). The product was triturated with diethyl ether. The solid obtained was purified by prep HPLC (C18 Phenomenex column, 10-90% MeCN in water 0.1% formic acid, 20 min gradient) to give the title compound as a white solid (140 mg, 42%). 1H NMR 400 MHz δ (DMSO-d6) (mixture of rotamers): 7.80 (0.5H, s), 7.76 (0.5H, s), 7.73 (1H, dd, J=8.8, 4.8 Hz), 7.67 (0.5H, d, J=7.5 Hz), 7.54 (0.5H, d, J=7.2 Hz), 7.50-7.31 (5H, m), 7.19-7.07 (3H, m), 5.28 (0.5H, quin, J=7.1 Hz), 5.21 (0.5H, quin, J=7.0 Hz), 3.48-3.35 (1H, m), 3.34-3.18 (4H, m), 3.10-2.87 (2H, m), 2.56-2.47 (1H, m), 1.47-1.40 (3H, m), LCMS (Method K): RT=2.96 min, [M+H]+=487, RT=3.00 min, [M+H]+=487 (mixture of rotamers)

Provenance & Evidence