3-Bromopyridine → N-(1-(4-(pyridin-3-yl)cyclohexyl)azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

Participants

Reaction Steps

Reaction of 4-(pyridin-3-yl)cyclohexanone (prepared by the reaction of 3-bromopyridine with 8-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,4-dioxa-spiro[4.5]dec-7-ene using the sequence described in Example 1 Step A-C) with N-(azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide (as prepared in Example 1 Step G) in the presence of TEA and NaBH(OAc)3 as described in Example 1, Step H afforded the product. 1H NMR (MeOD) δ: 8.62 (s, 1 H), 8.56 (s, 1 H), 8.43 (d, J=2.0 Hz, 1 H), 8.33 (dd, J=5.1, 1.5 Hz, 1 H), 8.04 (dd, J=8.8, 1.8 Hz, 1 H), 7.88 (d, J=8.8 Hz, 1 H), 7.77 (dt, J=7.8, 1.8 Hz, 1 H), 7.35 (dd, J=7.7, 5.2 Hz, 1 H), 4.51 (quin, J=7.1 Hz, 1 H), 4.28 (s, 2 H), 3.65-3.73 (m, 2 H), 2.95 (t, J=7.6 Hz, 2 H), 2.56-2.69 (m, 1 H), 2.43 (d, J=2.8 Hz, 1 H), 1.68-1.92 (m, 4 H), 1.49-1.62 (m, 4 H); ESI-MS (m/z): Calcd. For C25H27F3N6O: 484.22. found: 485 (M+H).

Provenance & Evidence