2-(1,1,2,2-tetrafluoroethoxy)benzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 10 mL flask was charged with (4-hydrazino-6-morpholin-4-yl-1,3,5-triazin-2-yl)-(4-trifluoromethoxyphenyl)amine (XV) (159 mg, 0.43 mmol), 4-(1,1,2,2-tetrafluoroethoxybenzaldehyde (142 μL, 0.86 mmol), and ethanol (5 mL) and the mixture was stirred at ambient temperature for 24 h. Water (5 mL) was added to the reaction mixture which was then extracted with EtOAc (3×5 mL). The combined organic extract was washed with brine (10 mL), dried over sodium sulfate, filtered, and concentrated under vacuum. Flash chromatography (silica gel, 10% EtOAc/cyclohexane) afforded compound 1 (167 mg, 68% yield): m.p. 203-206° C.; 1H NMR (CDCl3) δ 8.65 (s, 1H), 7.79 (s, 1H), 7.66-7.55 (m, 4H), 7.20-7.12 (m, 4H), 6.10-5.73 (tt, J1=53.1 Hz, J2=2.56 Hz, 1H), 3.86-3.75 (m, 8H). was then extracted with EtOAc (3×5 mL) The combined organic extract was washed with brine (10 mL) dried over sodium sulfate filtered concentrated under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 10 mL flask was charged with (4-hydrazino-6-morpholin-4-yl-1,3,5-triazin-2-yl)-(4-trifluoromethoxyphenyl)amine (XV) (159 mg, 0.43 mmol), 4-(1,1,2,2-tetrafluoroethoxybenzaldehyde (142 μL, 0.86 mmol), and ethanol (5 mL) and the mixture was stirred at ambient temperature for 24 h. Water (5 mL) was added to the reaction mixture which was then extracted with EtOAc (3×5 mL). The combined organic extract was washed with brine (10 mL), dried over sodium sulfate, filtered, and concentrated under vacuum. Flash chromatography (silica gel, 10% EtOAc/cyclohexane) afforded compound 1 (167 mg, 68% yield): m.p. 203-206° C.; 1H NMR (CDCl3) δ 8.65 (s, 1H), 7.79 (s, 1H), 7.66-7.55 (m, 4H), 7.20-7.12 (m, 4H), 6.10-5.73 (tt, J1=53.1 Hz, J2=2.56 Hz, 1H), 3.86-3.75 (m, 8H). was then extracted with EtOAc (3×5 mL) The combined organic extract was washed with brine (10 mL) dried over sodium sulfate filtered concentrated under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 10 mL flask was charged with (4-hydrazino-6-morpholin-4-yl-1,3,5-triazin-2-yl)-(4-trifluoromethoxyphenyl)amine (XV) (159 mg, 0.43 mmol), 4-(1,1,2,2-tetrafluoroethoxybenzaldehyde (142 μL, 0.86 mmol), and ethanol (5 mL) and the mixture was stirred at ambient temperature for 24 h. Water (5 mL) was added to the reaction mixture which was then extracted with EtOAc (3×5 mL). The combined organic extract was washed with brine (10 mL), dried over sodium sulfate, filtered, and concentrated under vacuum. Flash chromatography (silica gel, 10% EtOAc/cyclohexane) afforded compound 1 (167 mg, 68% yield): m.p. 203-206° C.; 1H NMR (CDCl3) δ 8.65 (s, 1H), 7.79 (s, 1H), 7.66-7.55 (m, 4H), 7.20-7.12 (m, 4H), 6.10-5.73 (tt, J1=53.1 Hz, J2=2.56 Hz, 1H), 3.86-3.75 (m, 8H). was then extracted with EtOAc (3×5 mL) The combined organic extract was washed with brine (10 mL) dried over sodium sulfate filtered concentrated under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 10 mL flask was charged with (4-hydrazino-6-morpholin-4-yl-1,3,5-triazin-2-yl)-(4-trifluoromethoxyphenyl)amine (XV) (159 mg, 0.43 mmol), 4-(1,1,2,2-tetrafluoroethoxybenzaldehyde (142 μL, 0.86 mmol), and ethanol (5 mL) and the mixture was stirred at ambient temperature for 24 h. Water (5 mL) was added to the reaction mixture which was then extracted with EtOAc (3×5 mL). The combined organic extract was washed with brine (10 mL), dried over sodium sulfate, filtered, and concentrated under vacuum. Flash chromatography (silica gel, 10% EtOAc/cyclohexane) afforded compound 1 (167 mg, 68% yield): m.p. 203-206° C.; 1H NMR (CDCl3) δ 8.65 (s, 1H), 7.79 (s, 1H), 7.66-7.55 (m, 4H), 7.20-7.12 (m, 4H), 6.10-5.73 (tt, J1=53.1 Hz, J2=2.56 Hz, 1H), 3.86-3.75 (m, 8H). was then extracted with EtOAc (3×5 mL) The combined organic extract was washed with brine (10 mL) dried over sodium sulfate filtered concentrated under vacuum