Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cyanoacetic acid | HCID 9740 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | HCID 118390088 | HCID 118390088 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 118389995 | HCID 118389995 | 18.1% |
Reaction Steps
To a suspension of 2-((1-methyl-1H-pyrazol-3-yl)amino)-4-((octahydrocyclopenta[c]pyrrol-5-yl)amino)pyrimidine-5-carbonitrile (165.2 mg, 0.5092 mmol) and 2-cyanoacetic acid (65 mg, 0.7642 mmol) in dichloromethane (20 mL) and N,N-dimethylformamide (5 mL) were added HATU (387.5 mg, 1.019 mmol) and N,N-diethylethanamine (103.5 mg, 1.023 mmol). The mixture was then stirred at rt for 1 h and then quenched with H2O (20 mL), and the resulted mixture was extracted with DCM/MeOH (10/1, 20 mL×3). The combined organic phases were washed with brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=10/1) to give the title compound as a white solid (36 mg, 18.06%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09403801B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-0c4e89030fd045b5bcbc5f342792a1ca |
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| Source note | uspto-grants-2016_08 |
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