HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1753851Generated: October 29, 2026
Triethylamine → 2,6-dichloro-N-(3-fluorobenzyl)-4-methyl-pyridine-3-carboxylic acid amide
https://huagongshe.com/reaction/1753851
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Fluorobenzylamine | HCID 66853 | — |
| Reactant | 2,6-Dichloro-4-methylpyridine-3-carboxylic acid | HCID 676121 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2,6-dichloro-N-(3-fluorobenzyl)-4-methyl-pyridine-3-carboxylic acid amide | HCID 86664313 | 74% |
Reaction Steps
To a solution of 17.4 g (84.4 mmol) of 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid in THF (340 ml) were added 10.6 ml (92.9 mmol) 3-fluorobenzylamine, 32.0 g (84.4 mmol) HATU and 35.0 ml (253.3 mmol) NEt3. The RM was then heated at 70° C. for 16. After dilution with EtOAc (350 ml) the mixture was washed with a 4M aq. NH4Cl sol., a 1M aq. NaHCO3 sol. and brine. The organic layer was dried over MgSO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 3:2) provided 19.5 g (62.3 mmol, 74%) 2,6-dichloro-N-(3-fluorobenzyl)-4-methyl-pyridine-3-carboxylic acid amide.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09168259B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-3b7ed9eb86d544fa99d2eb8c7d91932e |
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| Source note | uspto-grants-2015_10 |
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