Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methylamine | HCID 6329 | — |
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (+)-2-(2-Bromo-ethyl)-10-(3-hydroxy-phenyl)-6-methoxy-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione | HCID 68939448 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Ammonia | HCID 222 | — |
| Product | Diisopropyl Ether | HCID 7914 | — |
| Product | (3aSR,10RS)-10-(3-Hydroxy-phenyl)-6-methoxy-3a-methyl-2-(2-methylamino-ethyl)-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione | HCID 68937277 | — |
Reaction Steps
To a solution of 150 mg (3aSR,10RS)-2-(2-Bromo-ethyl)-10-(3-hydroxy-phenyl)-6-methoxy-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione (example 24) in 5 ml acetonitrile are added 66 mg sodium carbonate and 920 μl of a 2 M solution of methyl amine in tetrahydrofurane. The mixture is heated in a sealed tube to 140° C. for 3 h using a microwave reactor. 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 10:1:0.5) and trituration with diisopropylether, 60 mg of the title compound are obtained as a colorless solid. MS: m/z (MH+)=435.1
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08530493B2 |
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| Source dataset | uspto-grants-2013_09 |
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| ORD ID | ord-3432da1bd2764eeba9be487c123b8bdf |
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| Source note | uspto-grants-2013_09 |
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