Sodium Hydroxide → HCID 117601300, compound

Crude N-(4-(3,5-dimethylisoxazol-4-yl)-2-iodo-6-nitrophenyl)-N-ethyl-2,2,2-trifluoroacetamide (1.5 g, 3.1 mmol) was dissolved in 100 mL of methanol. To the mixture was added 1M sodium methoxide in methanol (15.5 mL, 15.5 mmol) and reaction stirred at room temperature until complete. Reaction was then quenched with 15 mL of 1M HCl or until pH is approximately neutral then diluted with aqueous ammonium chloride. Methanol was removed under reduced pressure and then remaining suspension was extracted with EtOAc. The solution was washed with water, brine then dried over sodium sulfate. Solvents were removed under reduced pressure the residue was then dissolved in 20 mL of ethanol and placed in a sealed pressure tube with stannous chloride (2.2 g, 11.62 mmol). The mixture was heated at 120° C. for 1 hour. Reaction mixture was cooled to room temperature. To the mixture was added 1M NaOH (10 mL) and the mixture was stirred at room temperature for 30 minutes. At this point the reaction mixture was diluted with water and extracted with EtOAc (3 times). The solution was washed with water, brine and dried over sodium sulfate. Solvents were removed under reduced pressure and crude product was purified by silica gel chromatography (Hexanes/EtOAc as the eluent) to provide 4-(3,5-dimethylisoxazol-4-yl)-N1-ethyl-6-iodobenzene-1,2-diamine (310 mg, 22%).

1. additionTo the mixture was added
2. customReaction
3. customwas then quenched with 15 mL of 1M HCl or until pH
4. additionis approximately neutral then diluted with aqueous ammonium chloride
5. customMethanol was removed under reduced pressure
6. extractionwas extracted with EtOAc
7. washThe solution was washed with water, brine
8. dry with materialthen dried over sodium sulfate
9. customSolvents were removed under reduced pressure the residue
10. dissolutionwas then dissolved in 20 mL of ethanol
11. temperatureThe mixture was heated at 120° C. for 1 hour
12. customReaction mixture
13. temperaturewas cooled to room temperature
14. stirringthe mixture was stirred at room temperature for 30 minutes
15. extractionextracted with EtOAc (3 times)
16. washThe solution was washed with water, brine
17. dry with materialdried over sodium sulfate
18. customSolvents were removed under reduced pressure and crude product
19. customwas purified by silica gel chromatography (Hexanes/EtOAc as the eluent)

ORD record

ord-f6e98102ebcb48299e108da9f58d3172

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09255089B2