Methanol → HCID 57955592, compound

Participants

Reaction Steps

To a solution of N-(azetidin-3-yl)-4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-2-fluoro-5-methoxybenzamide (100 mg, 0.19 mmol) in AcOH:DCM:MeOH (2.5 mL, 1:2:2) was added cyclopentanone (100 μL, 1.09 mmol), borane-pyridine complex (100 μL, 0.8 mmol), and left to stir for 3 h. The solvent was then removed and the product purified by reverse phase HPLC, free based, and lyophilized to yield a white solid (5.0 mg, 9%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.23-1.35 (m, 2H) 1.38-1.78 (m, 11H) 1.96 (br. s., 2H) 2.67 (br. s., 1H) 2.87 (t, J=7.33 Hz, 2H) 3.49 (t, J=7.33 Hz, 2H) 3.91 (s, 3H) 4.08 (t, J=13.77 Hz, 2H) 4.33-4.44 (m, 1H) 4.78-4.88 (m, 1H) 7.19 (d, J=6.57 Hz, 1H) 8.05 (s, 1H) 8.25 (d, J=13.39 Hz, 1H) 8.30 (s, 1H) 8.41 (dd, J=6.82, 3.03 Hz, 1H). [M+H] calc'd for C29H36F3N7O3, 588. found 588.

Provenance & Evidence