1-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-3-(trifluoromethyl)pyrrolidin-3-ol → Trifluoroacetic acid

Participants

Reaction Steps

1-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-3-(trifluoromethyl)pyrrolidin-3-ol (Preparation Hi) (245 mg, 0.610 mmol) and 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyaniline (Preparation A) (177 mg, 0.793 mmol) were combined and purified as per Example 16 to give 1-(2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylamino)-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-3-(trifluoromethyl)pyrrolidin-3-ol, TFA (second to elute, diastereomer 2) (51.1 mg, 0.073 mmol) as a white solid. LC-MS (M+H)+=589.1. 1H NMR (500 MHz, MeOD) δ ppm 7.96 (1H, d, J=1.83 Hz), 7.68 (1H, d, J=1.53 Hz), 7.19-7.27 (3H, m), 7.15 (1H, d, J=8.55 Hz), 7.04 (2H, t, J=8.70 Hz), 6.95 (1H, dd, J=8.55, 2.14 Hz), 4.10-4.21 (2H, m), 3.95-4.04 (3H, m), 3.61-3.69 (3H, m), 3.27-3.32 (1H, m), 3.08-3.20 (1H, m), 2.57 (1H, dddd, J=13.16, 8.74, 8.62, 4.58 Hz), 2.37 (1H, dt, J=12.89, 9.88 Hz), 2.18 (1H, dd, J=12.82, 6.41 Hz), 1.93-2.05 (1H, m). The relative stereochemistry of Example 28 was not determined

Provenance & Evidence