Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cyclopropanecarboxylic acid | HCID 15655 | — |
| 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 67517550 | HCID 67517550 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68379173 | HCID 68379173 | 94.1% |
Reaction Steps
To a solution of cyclopropyl carboxylic acid (0.20 g, 0.68 mmol) in DMF (2 mL) was added HATU (0.26 g, 0.68 mmol), Et3N (0.10 mL, 0.75 mmol) and the reaction mixture was allowed to stir at room temperature for 20 min. [1-(5-Hydrazinocarbonyl-pyridin-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester (0.20 g, 0.68 mmol) in DMF (1 mL) was added and the reaction allowed to stir at room temperature for 21 h. The mixture was diluted with water and extracted with EtOAc (3×100 mL). The combined extracts were washed with satd NaHCO3, brine and dried with MgSO4. The mixture was filtered and concentrated to give {1-[5-(N′-cyclopropane-carbonyl-hydrazinocarbonyl)-pyridin-2-yl]-cyclopropyl}-carbamic acid tert-butyl ester (0.23 g, 0.64 mmol) as a light brown solid, m/z 361.7 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08575360B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-704a4e2506aa4d278296f0af3a04bfd1 |
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| Source note | uspto-grants-2013_11 |
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