Cyclopentanone → HCID 16743931, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of cyclopentanone (68 mg, 0.8 mmol) in EtOH (1 ml) was added Br2 (15 mg, 0.09 mmol) at r.t., sealed and stirred for 5 mins. The yellow solution became clear colorless. (R)-1-(1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-phenylethyl)thiourea (20 mg, 0.04 mmol) was added to the reaction mixture and the mixture was heated at 75° C. for 16 hrs, then heated at 160° C. under microwave for 30 mins. The reaction mixture was purified by prep HPLC, desired fraction condensed under vacuum to give (R)-N-(1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-phenylethyl)-5,6-dihydro-4H-cyclopenta[d]thiazol-2-amine (6 mg, 27% yield). LCMS: 3.67 min [M+1] 566.40 (4 min gradient, MeOH/H2O 0.1% TFA); 1H NMR (400 MHz, CD3OD) δ ppm 2.32-2.42 (m, 2H), 2.55-2.66 (m, 2H), 2.69-2.80 (m, 2H), 3.88 (d, J=13.14 Hz, 1H), 4.28 (d, J=13.39 Hz, 1H), 6.27 (t, J=50.0 Hz, 1H), 6.61 (d, J=6.82 Hz, 2H), 6.97-7.09 (m, 4H), 7.24 (s, 1H) 7.34 (ddd, J=9.98, 2.02, 1.89 Hz, 1H), 7.41 (d, J=8.59 Hz, 1H) 7.79 (dd, J=8.59, 2.53 Hz, 1H), 8.38 (d, J=2.02 Hz, 1H).

Provenance & Evidence