Acetone → HCID 57955586, compound

Participants

Reaction Steps

The title compound was synthesized by solubilizing N-(azetidin-3-yl)-4-(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxybenzamide (33 mg, 0.07 mmol) in acetic acid: methanol: dichloromethane (1 mL of 1:2:2) and treatment with acetone (58 mg, 1.0 mmol), and borane-pyridine (100 μL, 0.8 mmol). The reaction was left to stir for 3 hours. The reaction solvent was removed and the final compound was purified by reverse phase HPLC and basified to give the free base (5.7 mg, 16% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.87 (d, J=6.06 Hz, 6H) 1.48-1.78 (m, 8H) 1.93 (br. s., 2H) 2.24-2.36 (m, 1H) 2.94 (t, J=6.82 Hz, 2H) 3.33 (s, 3H) 3.51 (t, J=6.82 Hz, 2H) 3.94 (s, 3H) 4.05 (t, J=14.02 Hz, 2H) 4.39 (q, J=6.99 Hz, 1H) 4.70-4.83 (m, 1H) 7.49 (d, 0H) 7.51 (s, 1H) 7.98 (s, 1H) 8.26 (s, 1H) 8.29 (d, 1H) 8.61 (d, J=6.82 Hz, 1H). [M+H] calculated for C28H37F2N7O3, 574. found 574.

Provenance & Evidence