Water → HCID 17965116, compound

HRID 1396146Notes

Reaction equation

HRID 1396146 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1.C(N(CC)C(C)C)(C)C.O>CN1CCCC1=O>[F:8][C:4]1[N:3]=[C:2]([NH:16][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 739342,6-DifluoropyridineHCID 754524-MethoxybenzylamineHCID 81531Diisopropylethylamine

Product 1

HCID 17965116HCID 17965116, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

To 2,6-difluoro-pyridine (39, 100 g, 869 mmol) in 500 mL of N-methylpyrrolidinone, 4-methoxy-benzylamine (40, 136 mL, 1.043 mol) and N,N-diisopropylethylamine (304 mL, 1.738 mol) are added. The reaction is stirred at 90° C. overnight, then poured into 8 L of water. The resulting precipitate is collected by filtration and washed with water, then taken up in ethyl acetate and washed with water. The organic layer is dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is triturated with heptane and collected by filtration to provide the desired compound (41, 151 g, 650 mmol, 74.8% yield).

Workup

  1. filtrationThe resulting precipitate is collected by filtration
  2. washwashed with water
  3. washwashed with water
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe resulting material is triturated with heptane
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-24303bac6daa417ab1f7fa24b6d6b9fc
Source dataset
uspto-grants-2014_12
Patent number
US08901118B2

Reaction notes

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