HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 118390064, compound
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 118390053 | HCID 118390053 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 118390064 | HCID 118390064 | 61.9% |
Reaction Steps
To a solution of 5-chloro-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(2-azaspiro[4.4]nonan-4-yl)pyrimidine-2,4-diamine (393 mg, 1.13 mmol), 2-cyanoacetic acid (240.83 mg, 2.83 mmol), HATU (429.63 g, 1.13 mmol) in a mixture of DCM and DMF (4/1 (v/v), 25 mL) was added Et3N (456.52 mg, 4.52 mmol) and the reaction mixture was stirred at rt for 3 hours. The resulting mixture was diluted with H2O (20 mL) and extracted with a mixture of DCM and MeOH (10/1 (v/v), 20 mL×3). The combined organic phases were washed with brine (50 mL), and dried over anhydrous Na2SO4, then concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH=100/1 to 20/1) to give the product as a white solid (290 mg, 61.8%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09403801B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-aa297efca8cb4a948c913bd05f2d87b3 |
| Source note | uspto-grants-2016_08 |