Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Acetohydrazide | HCID 14039 | — |
| 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 | 5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid | HCID 22556886 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58329558 | HCID 58329558 | — |
Reaction Steps
To a solution of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid (20 mg, 100 μmol) in dry N,N-dimethylformamide (700 μL) were added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (42 mg, 110 μmol), triethylamine (21 μL, 150 μmol), and acetohydrazide (10 μmol). The reaction was heated at 80° C. for 24 hours. The solvent was removed under reduced pressure. To the residue were added 1.5 mL of mixture of butanol and 1,2-dichloroethane (1:2.5) and 1.0 mL of sat. NaHCO3. The organic layer was separated and the solvent was removed under reduced pressure to afford N′-acetyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carbohydrazide (55). The crude was used for the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08563567B2 |
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| Source dataset | uspto-grants-2013_10 |
|---|
| ORD ID | ord-d1edf2c9c44b465a940264d2d3f33f53 |
|---|
| Source note | uspto-grants-2013_10 |
|---|
