HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetonitrile → Jnj-38893777
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | 4-Chloro-2-piperidin-1-yl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine | HCID 86615306 | — |
| Reactant | HCID 178517884 | HCID 178517884 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Jnj-38893777 | HCID 16742146 | 35% |
Reaction Steps
4-Chloro-2-piperidin-1-yl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine. To a solution of 2-piperidin-1-yl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-ol (435 mg, 1.11 mmol) in CH3CN (9 mL) was added POCl3 (0.41 mL, 4.43 mmol). After 1.5 h at 80° C., the mixture was cooled to rt, diluted with EtOAc, and quenched slowly with satd. aq. NaHCO3. The organic layers were combined, dried (Na2SO4), and concentrated. The crude residue was purified (FCC) to give the title compound (160 mg, 35%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08673895B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-b47b99acc18e474e8caea6b3aff953aa |
| Source note | uspto-grants-2014_03 |