HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 6-(9-((5-chloro-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)nicotinonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 6-Chloro-3-pyridinecarbonitrile | HCID 5152094 | — |
| Reactant | 5-chloro-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(3-azaspiro[5.5]undecan-9-yl) pyrimidine-2,4-diamine | HCID 118390069 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 6-(9-((5-chloro-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)nicotinonitrile | HCID 118390025 | 39.7% |
Reaction Steps
To a suspension of 5-chloro-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(3-azaspiro[5.5]undecan-9-yl) pyrimidine-2,4-diamine (0.11 g, 0.29 mmol) in a mixture of DCM and MeOH (5.0 mL/5.0 mL) were added 6-chloropyridine-3-carbonitrile (0.086 g, 0.62 mmol) and Et3N (0.10 mL, 0.72 mmol). The mixture was heated to reflux overnight and then concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=50/1) to afford the product as a light yellow solid (55 mg, 39%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09403801B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-4088088784e24c08a01e50de2a7afb52 |
| Source note | uspto-grants-2016_08 |