HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → HCID 25120679, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | 3,5-Difluorophenylacetic acid | HCID 145424 | — |
| Reactant | HCID 67521418 | HCID 67521418 | — |
| Catalyst | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 25120679 | HCID 25120679 | 15% |
Reaction Steps
3,5-Difluorophenylacetic acid (0.227 g, 1.30 mmol) was dissolved in DCM (5 mL), followed by addition of oxalyl chloride (137 μL, 1.56 mmol) and 2 drops of dry DMF. After 1 hour gas evolution had stopped and pyridine (106 μL, 1.30 mmol) was added, followed by addition of 3-amino-2-pyrrolidin-1-yl-3H-quinazolin-4-one. After stirring at RT for 5 minutes additional pyridine (212 μL, 2.60 mmol) was added. The reaction mixture was stirred overnight at RT. The mixture was diluted with EtOAc (20 mL), washed with 1 M HCl (20 mL), dried (MgSO4) and evaporated in vacuo. The crude product was subjected to column chromatography (EtOAc/Heptane) giving the title compound (0.073 g, 15%). LC-ESI-HRMS of [M+H]+shows 385,1485 Da. Calc. 385,147607 Da.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08178544B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-c41cf8c6ff374dc4857fe0af7a2b8aaf |
| Source note | uspto-grants-2012_05 |