Triethylamine → 3-(3-(4-(2-(Tetrahydrofuran-2-yl)-ethyl)-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine

Temperature

60 °C

To an anhydrous tetrahydrofuran (5 mL) solution of 3-ethynyl-pyridin-2-ylamine described in Manufacturing Example 1-2-3 (43.7 mg, 0.37 mmol) was added (4-(2-tetrahydrofuran-2-yl-ethyl) phenyl)-acetohydroximoyl chloride (300 mg, 1.12 mmol) described in Manufacturing Example 82-1-6 under nitrogen atmosphere at room temperature. Triethylamine (0.31 mL, 2.24 mmol) was then added dropwise and stirred for 2 hours at 60° C. The reaction mixture was partitioned into water and ethyl acetate at room temperature. The organic layer was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:9 then 3:7) to obtain the title compound (68 mg, 53%).

1. customdescribed in Manufacturing Example 82-1-6 under nitrogen atmosphere at room temperature
2. customThe reaction mixture was partitioned into water and ethyl acetate at room temperature
3. washThe organic layer was washed with water and saturated aqueous sodium chloride
4. dry with materialdried over anhydrous magnesium sulfate
5. customthe solvent was evaporated under a reduced pressure
6. customThe residue was purified by silica gel column chromatography (ethyl acetate

ORD record

ord-3c6ce090cbf04e729e603715113c06ca

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507530B2