6-Bromo-3,4-dihydroquinolin-2(1H)-one → (S)-6-(2-(2-amino-3-(4-(trifluoromethyl)phenyl)propylamino)thiazol-5-yl)-3,4-dihydroquinolin-2(1H)-one

Participants

Reaction Steps

The title compound was synthesized using a procedure similar to that shown in Scheme 1 with a coupling reaction between (S)-tert-butyl 1-(N-(5-bromothiazol-2-yl)-tert-butoxylcarbonylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate as shown in Scheme 10 and 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-one, which was prepared from commercially available 6-bromo-3,4-dihydroquinolin-2(1H)-one in a similar manner to the procedure shown in Scheme 1. MS m/z: 447 (M+1). 1H NMR (400 MHz, CD3OD): δ ppm 2.55-2.60 (m, 2H), 2.97 (t, J=7.63 Hz, 2H), 3.09 (dd, J=14.97, 7.34 Hz, 2H), 3.52 (d, J=6.85 Hz, 1H), 3.62 (d, J=3.72 Hz, 1H), 3.70 (m, 1H), 6.86 (d, J=8.22 Hz, 1H), 7.23-7.34 (m, 3H), 7.53 (d, J=8.02 Hz, 2H), 7.69 (d, J=8.02 Hz, 2H).

Provenance & Evidence