1,2-Dichloroethane → N-(4-(2-(1-Isopropyl-1,2,3,6-tetrahydropyridin-4-yl)-6-(4-(trifluoromethyl)-phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of N-(4-(2-(1,2,3,6-tetrahydropyridin-4-yl)-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide (109 mg, 0.195 mmol, Example 27), acetone (1 mL), 1,2-dichloroethane (6 mL) and DMF (0.5 mL) was added AcOH (one drop), and the mixture was heated at 50° C. with stirring for 10 min. The reaction mixture was left to reach room temperature, sodium triacetoxyborohydride (127 mg, 0.6 mmol, Aldrich) was added, and the stirring was continued for 2 h at room temperature. After the addition of acetone (1 mL) and sodium triacetoxyborohydride (127 mg, 0.6 mmol), the reaction mixture was stirred at room temperature for 1 h and evaporated under reduced pressure. The yellow residue was treated with 1N NaOH (5 mL) and extracted with EtOAc (2×20 mL). The combined EtOAc extracts were dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel column chromatography (gradient 0.5-5% (2M NH3 in MeOH) in EtOAc) afforded the title compound as a pale-yellow amorphous solid. MS (ESI, pos. ion.) m/z: 554 (M+1).

Provenance & Evidence