(2S)-2-(Trifluoromethyl)oxirane → HCID 178425491, compound

Participants

Reaction Conditions

Reaction Steps

Preparation of (S)-3-(trans-4-(3,5′-dichloro-6-((tetrahydro-2H-pyran-4-yl)methyl)amino-2,4′-bipyridin-2′-yl-amino)cyclohexylamino)-1,1,1-trifluoropropan-2-ol: To a solution of N2′-(trans-4-aminocyclohexyl)-3,5′-dichloro-N6-((2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl)-2,4′-bipyridine-2′,6-diamine (19 mg, 0.040 mmol) in 2-propanol (0.3 mL) was added (S)-(−)-3,3,3-trifluoro-1,2-epoxypropane (3.4 uL, 0.040 mmol). The mixture was stirred at 70° C. for 2 hr. The reaction mixture was concentrated. The resulting residue was purified by reverse phase HPLC and lyophilized to give 9.1 mg of (2S)-3-(trans-4-(3,5′-dichloro-6-((2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl)amino-2,4′-bipyridin-2′-yl-amino)cyclohexylamino)-1,1,1-trifluoropropan-2-ol as its TFA salt. LCMS (m/z): 590.5 (MH+), retention time=0.71 min; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.81-1.32 (m, 12 H) 1.33-1.66 (m, 4 H) 1.82-1.99 (m, 1 H) 1.99-2.21 (m, 4 H) 2.89-3.04 (m, 2 H) 3.04-3.19 (m, 2 H) 3.27 (d, J=2.35 Hz, 2 H) 4.40 (br. s., 1 H) 6.38 (s, 1 H) 6.55 (d, J=9.00 Hz, 1 H) 6.77 (br. s., 1 H) 6.91 (br. s., 1 H) 7.21 (br. s., 1 H) 7.48 (d, J=9.00 Hz, 1 H) 8.03 (s, 1H)

Provenance & Evidence