HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 118390084, 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 118390117 | HCID 118390117 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 118390084 | HCID 118390084 | 42.4% |
Reaction Steps
To a solution of 5-chloro-N4-methyl-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(7-azaspiro[4.5]decan-2-yl)pyrimidine-2,4-diamine (0.18 g, 0.479 mmol), 2-cyanoacetic acid (60.5 mg, 0.711 mmol) in a mixture of DCM (20 mL) and DMF (5 mL) were added HATU (335.2 mg, 0.882 mmol) and Et3N (169.4 mg, 1.674 mmol). After addition, the reaction mixture was stirred at rt overnight, then quenched with H2O (30 mL) and extracted with DCM (100 mL×3). The combined organic phases were washed with brine (100 mL), then dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=20/1) to give the title compound as a beige solid (83 mg, 39.1%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09403801B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-e580a28ef47745079dd8f46507a23ce3 |
| Source note | uspto-grants-2016_08 |