HCID 178421711, compound → HCID 86617879, compound

Participants

Reaction Steps

To a solution of tert-butyl (1R)-1-(6-{2-{benzyl[(2-methylcyclopropyl)methyl]amino}-6-[(isopropylsulfonyl)(methyl)amino]pyridin-4-yl}-3,4-dihydropyrimidin-4-yl)-1-methyl-2-phenylethylcarbamate from Step A above (49 mg, 0.07 mmol) in 2 mL toluene was added dichlorodicyanoquinone (24 mg, 0.11 mmol). The resulting solution was heated at 120 degrees for 30 min., then cooled to it and concentrated to dryness. Purification by reverse phase chromatography yielded tert-butyl (1R)-1-(6-{2-{benzyl[(2-methylcyclopropyl)methyl]amino}-6-[(isopropylsulfonyl)(methyl)amino]pyridin-4-yl}pyrimidin-4-yl)-1-methyl-2-phenylethylcarbamate, which was taken up in 1 mL 20% TFA in dichloromethane. The mixture was allowed to sit for 1 hour, and was concentrated to afford the title compound N-(4-{6-[(1R)-1-amino-1-methyl-2-phenylethyl]pyrimidin-4-yl}-6-{benzyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-methylpropane-2-sulfonamide. 1H NMR (400 MHz, d4-MeOH) δ 9.29 (s, 1H), 7.66-7.65 (m, 1H), 7.31-7.21 (m, 8H), 7.02-7.01 (m, 2H), 6.96-6.93 (m, 2H), 4.98-4.60 (m, 2H), 3.83-3.66 (m, 2H), 3.38 (s, 3H), 3.35-3.25 (m, 4H), 1.81 (s, 3H), 1.16 (d, J=6.8 Hz), 0.96 (dd, J=6 Hz, J=1.8 Hz, 3H) 0.90-0.82 (m, 1H), 0.70-0.62 (m, 1H), 0.45-0.40 (m, 1H), 0.28-0.24 (m, 1H); LCMS [M+H]=599.1.

Provenance & Evidence