Ethanol → HCID 74408212, compound

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).

1. extractionwas then extracted with EtOAc (3×5 mL)
2. extractionThe combined organic extract
3. washwas washed with brine (10 mL)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under vacuum

ORD record

ord-038d182fe7bc4401909d88a38e454dd8

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08067588B2