Salicylaldehyde oxime → HCID 58387695, compound

Temperature

82 °C

A sealed tube was charged with Copper(I) oxide (5.82 μL, 0.244 mmol), salicylaldoxime (134 mg, 0.975 mmol), 3-chloro-1H-pyrazole (500 mg, 4.88 mmol), Cs2CO3 (3178 mg, 9.75 mmol) and Part A compound of Example 1(150 mg, 7.32 mmol) and MeCN (4.877 mL). The tube was purged with N2 and the reaction stirred at 82° C. for 5 h. After cooling to RT, the mixture was diluted with CH2Cl2 (10 mL) and filtered through a pad of CELITE®. The filtrate was concentrated and purified by flash chromatography (silica gel, hexanes:EtOAc, 100:0 to 50:50) to afford 420 mg (38% yield) of the title compound as a brown solid: 1H NMR (500 MHz, CD3OD) δ 9.88 (1H, s), 8.34 (1H, s), 7.62 (1H, s), 7.07 (1H, s), 2.48 (3H, s). HPLC retention time 2.923 min., LCMS (ES): m/z 227 [M+H]+.

1. customThe tube was purged with N2
2. temperatureAfter cooling to RT
3. additionthe mixture was diluted with CH2Cl2 (10 mL)
4. filtrationfiltered through a pad of CELITE®
5. concentrationThe filtrate was concentrated
6. custompurified by flash chromatography (silica gel, hexanes:EtOAc, 100:0 to 50:50)

ORD record

ord-bba66a26e13c4c139160dc1f092c121b

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344160B2