1,4-Dioxaspiro[4.5]decan-8-one → N-(1-(4-hydroxy-4-(isothiazol-5-yl)cyclohexyl)azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

Participants

Reaction Steps

Reaction of 4-hydroxy-4-(isothiazol-5-yl)cyclohexanone (prepared by the reaction of 5-bromoisothiazole with 1,4-dioxaspiro[4.5]decan-8-one using the sequence described in Example 24 Step A-B) 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 (CHLOROFORM-d) δ: 8.61 (s, 1 H), 8.45-8.51 (m, 1 H), 8.35 (d, J=1.8 Hz, 1 H), 7.92-7.98 (m, 1 H), 7.87-7.92 (m, 1 H), 7.04 (d, J=1.8 Hz, 1 H), 4.62 (t, J=6.8 Hz, 1 H), 4.21-4.31 (m, 2 H), 3.97-4.09 (m, 2 H), 3.79-3.88 (m, 1 H), 3.13 (q, J=7.3 Hz, 6 H), 2.05-2.26 (m, 2 H), 1.78 (d, J=12.9 Hz, 6 H), 1.35 (t, J=7.3 Hz, 9 H); ESI-MS (m/z): Calcd. For C23H25F3N6O2S: 506.17. found: 507 (M+H).

Provenance & Evidence