Triethylamine → HCID 66937075, compound

HRID 1623320Notes

Reaction equation

HRID 1623320 reaction equation
F[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[N:3]=1.[CH3:10][C:11]1([CH2:17][NH2:18])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(N(CC)CC)C>CN1C(=O)CCC1.CCOC(C)=O.[Cl-].[Na+].O.O>[F:8][C:7]1[C:2]([NH:18][CH2:17][C:11]2([CH3:10])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[N:3][C:4]([F:9])=[CH:5][CH:6]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 27832882,3,6-TrifluoropyridineHCID 54165201(4-Methyloxan-4-yl)methanamine

Product 1

HCID 66937075HCID 66937075, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
70 °C

Procedure

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.

Workup

  1. customwas allowed to ambient temperature
  2. washThe separated organic layer was washed with brine (1×), 0.3N aqueous HCl (2×), saturated aqueous NaHCO3 solution (1×), brine (1×)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered off
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ba110b17a734a15a1071c98564eb487
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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