HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → 4'-({4-[4-(1-Methylethoxy)phenyl]-5-oxo-7-propyl-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate | HCID 10020734 | — |
| Reactant | N-[4-(1-methylethoxy)phenyl]-1H-pyrazol-5-amine | HCID 67009388 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | N,N-Diethylaniline | HCID 7061 | — |
| Product | 4'-({4-[4-(1-Methylethoxy)phenyl]-5-oxo-7-propyl-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrile | HCID 67009111 | 89% |
Reaction Steps
N-[4-(1-Methylethoxy)phenyl]-1H-pyrazol-5-amine (0.37 g) and a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (0.051 mL) and ethyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (1.2 g) in diethylaniline (5 mL) were stirred at 180° C. for 1 hr. The mixture was allowed to cool, ethyl acetate and water were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (0.76 g, 89%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08592431B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-e8c9f62b72574521afe3184dd64446ab |
| Source note | uspto-grants-2013_11 |