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 89581171 | HCID 89581171 | — |
| Reactant | HCID 178425242 | HCID 178425242 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178426848 | HCID 178426848 | 56% |
Reaction Steps
A mixture of 4-(1-(p-tolyloxy)ethyl)benzoic acid (30 mg, 0.12 mmol), o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (67 mg, 0.18 mmol), triethylamine (0.1 mL) and dichloromethane (15 mL) were stirred at 25° C. for half an hour. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (22 mg, 0.14 mmol) was added. The mixture was stirred at 25° C. for 12 hours. The resultant mixture was washed with water (30 mL), dried over sodium, filtered, and concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-(p-tolyloxy)ethyl)benzamide as a white solid (26 mg, 56%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09206128B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-0bdabdbf2c734c07b6d77cda5e20f565 |
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| Source note | uspto-grants-2015_12 |
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