Ammonia → HCID 58964644, compound

Temperature

-78 °C

To a 25 mL recovery flask was added 2-(4,6-dichloro-[1,3,5]triazin-2-yloxy)-N-(3-trifluoromethyl-phenyl)-acetamide (293 mg, 0.798 mmol, 1.0 eq.) and a stirbar. THF (7 mL) was added and the resulting solution was cooled to −78° C. Ammonia (NH3, 2.0 M in EtOH, 2.00 mL, 6 mmol, 5 eq.) was added in 400 μl aliquots until the reaction was complete by LC/MS analysis. The reaction mixture was diluted with EtOAc (50 mL) and washed with H2O (1×50 mL) and brine (1×50 mL). The combined aqueous phases were extracted with EtOAc (2×25 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated to give an off-white solid. The solid washed with EtOAc to give 2-(4-Amino-6-chloro-[1,3,5]triazin-2-yloxy)-N-(3-trifluoromethyl-phenyl)-acetamide as a white solid (70 mg, 25%). LC/MSD (HP Series 1100 MSD) Expected MW: 357.04, Observed M−H, 358.1, Retention time: 1.37. 1H-NMR, DMSO-d6, Varian 400 MHz δ 10.54 (s, 1H), 8.10-8.07 (m, 2H), 8.02 (s, 1H), 7.78 (d, 1H), 7.57 (t, 1H), 7.43 (d, 1H), 4.96 (s, 2H) ppm.

1. washwashed with H2O (1×50 mL) and brine (1×50 mL)
2. extractionThe combined aqueous phases were extracted with EtOAc (2×25 mL)
3. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customto give an off-white solid
7. washThe solid washed with EtOAc

ORD record

ord-30746f94575544338bde09c572b05856

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07816353B2