(Dimethyl sulfide)trihydroboron → HCID 57955649, compound

Participants

Reaction Conditions

Reaction Steps

The title compound was synthesized by solubilizing 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-methoxybenzoic acid (0.36 mmol) in THF (20 mL), and adding borane-dimethylsulfide (2.0M, 1.8 mL, 3.6 mmol) slowly. The solution was stirred for 18 h and then heated to 50° C. for 2 hours. The reaction mixture was then washed with water (×2), brine, and the solvent evaporated. The final compound was purified by reverse phase HPLC and basified to give the free base (8.1 mg, 5% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.37-1.96 (m, 8 H) 2.82 (s, 3 H) 3.48 (t, J=13.39 Hz, 2 H) 3.78 (t, J=12.00 Hz, 2 H) 3.86 (s, 3 H) 4.43 (d, 2 H) 4.84 (t, J=7.83 Hz, 1 H) 5.07 (t, J=5.81 Hz, 1 H) 6.82 (d, J=8.34 Hz, 1 H) 6.95 (s, 1 H) 7.31 (s, 1 H) 7.66 (s, 1 H) 8.21 (d, J=8.08 Hz, 1 H). [M+H] calculated for C21H27F2N5O2, 420; found 420.

Provenance & Evidence