Sulfuric acid magnesium salt (1:1) → HCID 118468284, compound

HRID 629475Notes

Reaction equation

HRID 629475 reaction equation
[CH2:1]([C:3]1[C:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:24]=[CH:23][N:22]([CH3:25])[N:21]=3)=[CH:16][CH:15]=2)=[CH:11][C:6]([C:7](OC)=[O:8])=[C:5]([CH:26]=O)[CH:4]=1)[CH3:2].[O:28]1[CH2:32][CH2:31][CH2:30][CH:29]1[CH2:33][NH2:34].S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:6](=[CH:11][C:12]=1[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]3[CH:24]=[CH:23][N:22]([CH3:25])[N:21]=3)=[CH:16][CH:15]=1)[C:7](=[O:8])[N:34]([CH2:33][CH:29]1[CH2:30][CH2:31][CH2:32][O:28]1)[CH2:26]2)[CH3:2]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 253298TetrahydrofurfurylamineHCID 118468296HCID 118468296, compound

Product 1

HCID 118468284HCID 118468284, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-ethyl-2-formyl-5-(4-(1-methyl-1H-pyrazol-3-yl)benzyl)benzoate (0.11 g), (tetrahydrofuran-2-yl)methanamine (0.03 g) and anhydrous magnesium sulfate (0.07 g) in THF (3.00 mL) was stirred overnight at room temperature. The insoluble substance was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was diluted with acetic acid (3.00 mL), sodium triacetoxyborohydride (0.09 g) was added thereto, and the mixture was stirred overnight at room temperature. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate/hexane), and crystallized from ethyl acetate/hexane to give the title compound (0.03 g).

Workup

  1. customThe insoluble substance was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was diluted with acetic acid (3.00 mL), sodium triacetoxyborohydride (0.09 g)
  4. additionwas added
  5. stirringthe mixture was stirred overnight at room temperature
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)
  11. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-51f3315fa1c5496b8880dfcb1f24dd16
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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