(R)-6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-amine hydrochloride → (R)-3-hydroxy-1-methyl-2-oxo-N-(6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl)-1,2-dihydroquinoline-4-carboxamide

Participants

Reaction Steps

Following the procedure described for Example 3, Example 192 (4 mg, 9.94 μmol, 20% yield) was prepared as an off-white powder by using 3-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-4-carbonyl chloride (see Example 3C) and (R)-6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-amine (Intermediate 15). LCMS=2.07 min, [M+1]=403.1 (Method A); Orthogonal HPLC (150×4.6 mm 3.5 μm, 254 nm): Sunfire {RT=9.47 min, 98%}; Xbridge {RT=8.63 min, 92%}. 1H NMR (500 MHz, MeOD) δ ppm 7.80 (1 H, s), 7.64 (1 H, d, J=8.3 Hz), 7.48-7.57 (3 H, m), 7.44 (1H, d, J=8.0 Hz), 7.31 (1 H, t, J=7.4 Hz), 5.76 (1 H, t, J=7.4 Hz), 3.81 (3 H, s), 3.08-3.18 (1 H, m), 2.98-3.06 (1 H, m), 2.67-2.74 (1 H, m), 2.05-2.13 (1 H, m).

Provenance & Evidence