HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonium Chloride → 5-(7-(Cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 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-(7-(Cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxylic acid | HCID 58314230 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 5-(7-(Cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxamide | HCID 58314581 | 105.2% |
Reaction Steps
To 5-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxylic acid (40 mg, 0.122 mmol), HATU (70 mg, 0.183 mmol), HOBt (4 mg, 0.024 mmol) and DIEA (85 μL, 0.488 mmol) in 2 mL of DMF was added ammonium chloride (20 mg, 0.366 mmol). The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate washed with saturated NaHCO3 solution, brine, dried over MgSO4, filtered, and evaporated to dryness to provide 42 mg of 5-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxamide (100%). LCMS (M+1=328).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09303033B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-b4837c29dedc42d3b51d9132d1867a95 |
| Source note | uspto-grants-2016_04 |