Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium dithionate | HCID 146045 | — |
| Reactant | Methyl 2-(3-formylphenyl)acetate | HCID 11819590 | — |
| Reactant | (R)-(1-(5,6-Diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride | HCID 89854051 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 178499408 | HCID 178499408 | — |
Reaction Steps
Into a vial was added methyl 2-(3-formylphenyl)acetate (98 mg, 0.55 mmol), (R)-(1-(6-amino-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (Intermediate 1, Step 3) (140 mg, 0.45 mmol) and ethanol (1.5 mL). Then sodium dithionate (388 mg, 2.23 mmol) and water (0.5 mL) were added to the mixture. The vial was sealed. The reaction mixture was heated to 110° C. for 18 h. The solution was cooled to room temperature. Triethylamine (0.15 mL, 1.1 mmol) was added and the solution was stirred at 100° C. for 18 h. A sample (0.8 mL) of the solution was removed and concentrated to dryness, and the resulting residue was purified via HPLC to afford the title compound. MS (ESI+) (M+H) 448.2; HPLC retention time 2.28 min (Method A).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09296745B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-3f9a2534368a4eb3b118866f79b374cd |
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| Source note | uspto-grants-2016_03 |
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