4-Methylmorpholine → HCID 86698907, compound

Participants

Reaction Steps

To a solution of 2-[(5R,6S,8S)-8-amino-5-methyl-6-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-3-yl]propan-2-ol (6.7 mg, 0.023 mmol) in N,N-dimethylformamide (195 μL) was added (6S)-6′-oxo-5,6′,7,7′-tetrahydrospiro[cyclopenta[b]pyridine-6,5′-pyrrolo[2,3-d]pyrimidine]-3-carboxylic acid (5.5 mg, 0.019 mmol), 1-hydroxy-7-azabenzotriazole (0.2 mg, 0.002 mmol), N-methylmorpholine (10.7 μL, 0.097 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.5 mg, 0.023 mmol). The mixture was stirred 2 h. Water was added, and the mixture was purified by reverse phase chromatography (C-18, 85% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) giving the title compound (1.4 mg). HRMS 550.2546 (M+1). NMR (500 MHz, CD3OD): δ 8.95 (s, 1H); 8.70 (s, 1H); 8.22 (s, 1H); 8.15 (s, 1H); 7.41−7.27 (m, 5H); 6.86 (s, 1H); 5.43 (dd, J=10.7, 7.5 Hz, 1H); 5.04 (dd, J=7.0, 4.8 Hz, 1H); 3.70−3.41 (m, 5H); 2.70−2.67 (m, 1H); 2.52−2.49 (m, 1H); 1.64 (d, J=13.6 Hz, 6H); 1.32 (d, J=6.4 Hz, 3H).

Provenance & Evidence