HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Chloronicotinic acid → 5-Acetyl-1-(1,3-benzodioxol-5-yl)-8-{[(2-chloropyridin-3-yl)carbonyl]amino}-4,5-dihydro-1h-pyrazolo[4,3-c]quinoline-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Chloronicotinic acid | HCID 76258 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| 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-Acetyl-8-amino-1-(1,3-benzodioxol-5-yl)-4,5-dihydro-1h-pyrazolo[4,3-c]quinoline-3-carboxamide acetate | HCID 10138855 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-Acetyl-1-(1,3-benzodioxol-5-yl)-8-{[(2-chloropyridin-3-yl)carbonyl]amino}-4,5-dihydro-1h-pyrazolo[4,3-c]quinoline-3-carboxamide | HCID 10143215 | 19% |
Reaction Steps
The title material of Example 17 (100 mg, 0.00025 mol) was dissolved in DMF (2 mL), and to the solution was added 2-Chloronicotinic acid (40 mg, 0.00025 mol), HATU (144 mg, 0.00038 mol), and DIEA (49 mg, 0.00038 mol). The reaction was blanketed with argon and stirred at room temperature for 18 hours. The solution was concentrated in vacuo, and the resulting solid were washed with water and then filtered. The product was then recrystallized from ethanol, and isolated by vacuum filtration. 25 mg. (MW=530.93, 19% yield). LC/MS m/z=531.7 (m+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07211597B2 |
| Source dataset | uspto-grants-2007_05 |
| ORD ID | ord-f406e9171fef4485be4c59aa2b741cc2 |
| Source note | uspto-grants-2007_05 |