Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | HCID 86629209 | HCID 86629209 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 24803740 | HCID 24803740 | 64% |
Reaction Steps
Dissolve methanesulfonic acid (R)-1-{4-[2-(4-chloro-phenyl)-7-oxo-7H-thieno[2,3-c]pyridin-6-yl]-2-methoxy-phenyl}-pyrrolidin-3-yl ester (0.504 g, 0.952 mmol) in 2 M dimethylamine in THF (10 mL). Stir the mixture at 75° C. overnight in a sealed pressure tube. Dilute the mixture with EtOAc (50 mL) and wash with saturated NaHCO3 (2×20 mL) and brine (20 mL). Dry the solution with Na2SO4, filter, and concentrate. Purify the crude material by chromatograghy, eluting with 2% NH3—H2O/50% CH3OH/EtOAc to give 0.293 g (64%) of 2-(4-chloro-phenyl)-6-[4-((S)-3-dimethylamino-pyrrolidin-1-yl)-3-methoxy-phenyl]-6H-thieno[2,3-c]pyridin-7-one.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08263772B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-fc30fc85e6ce46879c492b760bbc0115 |
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| Source note | uspto-grants-2012_09 |
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