Ethanol → HCID 178516615, compound

Intermediates J1 and J2 were prepared essentially according to the procedure described in US Patent Publication No.: US 2006/0041131 A1. Sodium metal (6.64 g, 289 mmol) was added to EtOH (450 mL) and stirred for 40 min until all was dissolved. Next, ethyl acrylate (24.12 ml, 159 mmol) and 3-aminopyrazole (12.00 g, 144 mmol) were added, and the reaction mixture was heated to reflux for 3 h. The reaction mixture was cooled to room temperature, filtered, and the collected solids rinsed with excess EtOH. The isolated solids were dissolved in water (˜300 mL), which was cooled with and ice water bath. The aqueous mixture was acidified to pH=1-2 with concentrated HCl. The resulting precipitate was filtered and rinsed with excess water. The isolated solid was dried in a vacuum oven at 30° C. over the weekend to afford the title compound (J1) as an off-white solid (13.5 g, 62%). LRMS m/z (M+H+H2O) 170.1 found, 152.0 required.

1. customIntermediates J1 and J2 were prepared essentially
2. dissolutionall was dissolved
3. temperaturethe reaction mixture was heated
4. temperatureto reflux for 3 h
5. filtrationfiltered
6. washthe collected solids rinsed with excess EtOH
7. dissolutionThe isolated solids were dissolved in water (˜300 mL)
8. temperaturewhich was cooled with and ice water bath
9. filtrationThe resulting precipitate was filtered
10. washrinsed with excess water
11. customThe isolated solid was dried in a vacuum oven at 30° C. over the weekend

ORD record

ord-78dd128937704ce980bd0886d0a97466

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957077B2