Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2,3,6-Trifluoropyridine | HCID 2783288 | — |
| Reactant | (4-Methyloxan-4-yl)methanamine | HCID 54165201 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 66937075 | HCID 66937075 | — |
Reaction Steps
A mixture of 2,3,6-trifluoropyridine (858 mg, 6.45 mmol), (4-methyltetrahydro-2H-pyran-4-yl)methanamine (1000 mg, 7.74 mmol) and triethylamine (2.158 mL, 15.48 mmol) in NMP (16 mL) was heated at 70° C. for 1 hr. The reaction mixture was allowed to ambient temperature and was diluted with EtOAc (˜100 mL), brine (˜50 mL) and water (˜50 mL). The separated organic layer was washed with brine (1×), 0.3N aqueous HCl (2×), saturated aqueous NaHCO3 solution (1×), brine (1×), dried over Na2SO4, filtered off and concentrated in vacuo to provide crude 3,6-difluoro-N-((4-methyltetrahydro-2H-pyran-4-yl)methyl)pyridin-2-amine as a colorless oil, which was directly used in the next reaction without further purification. Yield: 1.4 g. LCMS (m/z): 243.1 [M+H]+; Retention time=0.86 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08778951B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-2ba110b17a734a15a1071c98564eb487 |
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| Source note | uspto-grants-2014_07 |
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