Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| 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 69672221 | HCID 69672221 | — |
| Reactant | HCID 178482760 | HCID 178482760 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178425129 | HCID 178425129 | 49% |
Reaction Steps
A mixture of 4,6-Dimethyl-3-((methylamino)methyl)pyridin-2-ol (28 mg, 0.17 mmol), 3-chloro-4-(2-cyano-3-(pyrimidin-4-yl)phenoxy)benzoic acid (50 mg, 0.14 mmol), triethylamine (42 mg, 0.42 mmol) and 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (65 mg, 0.17 mmol) in dichloromethane (20 mL) was stirred at room temperature for 15 hours. Water (20 mL) was added to the mixture. The organic phase was separated and concentrated in vacuo to give a residue. The residue was further purified by preparative-HPLC to provide 3-chloro-4-(2-cyano-3-(pyrimidin-4-yl)phenoxy)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-N-methylbenzamide (Compound I-17) as a white solid (34 mg, 49%). LRMS (M+H+) m/z: calcd 499.1. found 499. HPLC purity (214 nm): 94%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09206128B2 |
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| Source dataset | uspto-grants-2015_12 |
|---|
| ORD ID | ord-a47860c749c64060bcac341813c9636a |
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| Source note | uspto-grants-2015_12 |
|---|
