HCID 71278256, compound → HCID 71268737, compound

Participants

Reaction Steps

tert-Butyl[(4aR,6R,8aS)-6-(fluoromethyl)-8a-(2-fluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]carbamate (C26) was converted to the product according to the general procedure for the synthesis of (4aR,6R,8aS)-8a-(2-fluorophenyl)-6-[(propan-2-yloxy)methyl]-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine, trifluoroacetate salt (2) in Example 2. In this case, the reversed-phase HPLC purification was carried out using a different system (Column: Waters XBridge C18, 5 μm; Mobile phase A: 0.03% ammonium hydroxide in water (v/v); Mobile phase B: 0.03% ammonium hydroxide in acetonitrile (v/v); Gradient: 25% to 100% B). Yield: 3 mg, 0.01 mmol, 10%. LCMS m/z 299.1 (M+1). 1H NMR (600 MHz, DMSO-d6) δ 1.43-1.48 (m, 1H), 1.63-1.72 (m, 1H), 2.64-2.72 (m, 2H), 2.75-2.80 (m, 1H), 3.60 (d, J=11.0 Hz, 1H), 3.76-3.85 (m, 1H), 3.96 (dd, J=10.8, 1.5 Hz, 1H), 4.30-4.48 (m, 2H), 6.13 (br s, 2H), 7.14-7.22 (m, 2H), 7.30-7.36 (m, 2H).

Provenance & Evidence