Acetic Acid → HCID 57955543, compound

Participants

Reaction Steps

To a solution of 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)-3-methoxy-N-(1-(piperidin-4-yl)azetidin-3-yl)benzamide (13 mg, 0.023 mmol) in MeOH (2.5 mL) was added AcOH (0.03 mL), cyclopropane aldehyde (3 μL, 0.034 mmol), borane-pyridine complex (10 μL, 0.08 mmol), and left to stir overnight. The solvent was then removed and the product purified by reverse phase HPLC, free based, and lyophilized to yield a white solid (6.4 mg, 44%). 1H NMR (400 MHz, DMSO-d6) δ ppm −0.03-0.14 (m, 3 H) 0.34-0.51 (m, 2 H) 0.80 (s, 1 H) 1.17 (d, J=2.53 Hz, 2 H) 1.60 (br. s., 6 H) 1.71 (br. s., 2 H) 1.94 (br. s., 5 H) 2.13 (d, J=6.32 Hz, 2 H) 2.82 (br. s., 2 H) 2.96 (t, J=7.20 Hz, 2 H) 3.52 (t, J=7.20 Hz, 2 H) 3.92 (s, 1 H) 4.05 (t, J=14.02 Hz, 2 H) 4.38-4.50 (m, 1 H) 4.70-4.82 (m, 1 H) 7.41-7.58 (m, 2 H) 7.98 (s, 1 H) 8.22-8.33 (m, 2 H) 8.61 (d, J=6.57 Hz, 1 H). [M+H] calc'd for C33H44F2N8O3, 638; found 638.

Provenance & Evidence