Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 6-Chloro-3-pyridinecarbonitrile | HCID 5152094 | — |
| Reactant | HCID 67277578 | HCID 67277578 | — |
| Solvent | 1,3-Dimethyl-2-imidazolidinone | HCID 6661 | — |
| Product | HCID 67278473 | HCID 67278473 | 47.2% |
Reaction Steps
To a solution of rel-1-[(3R,4S)-3-methyl-4-piperidinyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (20 mg) in 1,3-dimethyl-2-imidazolidinone (0.5 mL) were added 6-chloronicotinonitrile (20 mg) and triethylamine (41 μl), The mixture was stirred at 160° C. for 2 hours. The mixture was extracted with chloroform and washed with water. The extract was dried over MgSO4, filtrated and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10) to give rel-6-[(3R,4S)-3-methyl-4-(2-oxo-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(2H)-yl)-1-piperidinyl]nicotinonitrile (13 mg) as a white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08163767B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-05b8afeeca314a9ea86f11acc7eb1afb |
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| Source note | uspto-grants-2012_04 |
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