HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Ammonia
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Azetidine | HCID 10422 | — |
| Reactant | (3aSR,10RS)-2-(2-Bromo-ethyl)-6-chloro-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione | HCID 68940637 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Ammonia | HCID 222 | — |
| Product | Diisopropyl Ether | HCID 7914 | — |
| Product | (3aSR,10RS)-2-(2-Azetidin-1-yl-ethyl)-6-chloro-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione | HCID 68943114 | — |
Reaction Steps
To a solution of 200 mg (3aSR,10RS)-2-(2-Bromo-ethyl)-6-chloro-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione (example 26) in 5 ml acetonitrile are added 87 mg sodium carbonate and 83 μl azetidine. The mixture is heated to reflux for 4 h. Water is added and the mixture is extracted with ethyl acetate. The organic layer is dried with magnesium sulfate. The solvent is removed under reduced pressure. After column chromatography (silica gel; ethyl acetate, methanol, ammonia 10:0.2:0.1) and trituration with diisopropylether, 61 mg of the title compound are obtained as a colorless solid. MS: m/z (MH+)=465.1
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08530493B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-6f2bf8e3e0144ac1944b28ff8dae6058 |
| Source note | uspto-grants-2013_09 |