Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (1-(5,6-Diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride | HCID 89853790 | — |
| Reactant | Ethyl 2-cyclopropylpyrimidine-4-carbimidate | HCID 89854162 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 178419984 | HCID 178419984 | — |
Reaction Steps
To a solution of (1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride (18 mg, 0.06 mmol) and acetic acid (55 μL, 0.96 mmol) in ethanol (0.5 mL) was added triethylamine (17 μL, 0.12 mmol) followed by ethyl 2-cyclopropylpyrimidine-4-carbimidate (11.5 mg, 0.06 mmol) dissolved in ethanol (0.5 mL). The reaction mixture was heated to 70° C. for 1.25 h. The solvent was removed under reduced pressure. The residue was suspended in ethyl acetate and the undissolved solids were filtered off. The filtrate was washed with a saturated aqueous solution of ammonium chloride, washed with a saturated aqueous solution of sodium bicarbonate, and washed with brine. The organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via HPLC to afford the title compound. MS (ESI+) (M+H) 427.1; HPLC retention time 2.0183 (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-a22db86a9f0c41c993bf0a509ed7154a |
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| Source note | uspto-grants-2016_03 |
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