2-Bromothiazole → N-((2S,3S,E)-2-amino-3-(4-(trifluoromethyl)phenyl)hex-4-enyl)-5-(isoquinolin-6-yl)thiazol-2-amine

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Reaction Steps

The title compound was synthesized in a manner similar to that described for Example 35 using a nosyl aziridine intermediate to introduce the (2S,3S,E)-2-amino-3-(4-(trifluoromethyl)phenyl)hex-4-enylamine side chain to make the bromothiazole intermediate that was coupled with isoquinolin-6-ylboronic acid. The nosyl aziridne was prepared in a similar manner to that described for Example 17 starting with (2S,3S,E)-2-amino-3-(4-(trifluoromethyl)phenyl)hex-4-en-1-ol which was prepared as shown in Scheme 35. MS m/z: 469 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 9.12 (s, 1H) 8.38 (d, J=5.87 Hz, 1H) 8.03 (d, J=8.80 Hz, 1H) 7.86 (dd, J=8.61, 1.76 Hz, 1H) 7.70-7.80 (m, 2H) 7.65 (t, J=4.01 Hz, 3H) 7.50 (d, J=8.22 Hz, 2H) 5.63-5.83 (m, 2H) 3.65 (dd, J=13.11, 2.74 Hz, 1H) 3.37-3.44 (m, 2H) 3.21-3.30 (m, 1H) 1.73 (dd, J=6.26, 1.37 Hz, 3H).

Provenance & Evidence