Methylammonium trifluoroacetate → 3-(1-adamantyl)-4-methyl-5-propyl-4H-1,2,4-triazole

HRID 2054559Notes

Reaction equation

HRID 2054559 reaction equation
[C:1]12([C:11]3O[C:13]([CH2:16][CH2:17][CH3:18])=[N:14][N:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.FC(F)(F)C([O-])=O.[CH3:26][NH3+:27]>>[C:1]12([C:11]3[N:27]([CH3:26])[C:13]([CH2:16][CH2:17][CH3:18])=[N:14][N:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

3

Reactant 2

HCID 15260452Methylammonium trifluoroacetateHCID 596561392-(1-Adamantyl)-5-propyl-1,3,4-oxadiazole

Product 1

HCID 596561303-(1-adamantyl)-4-methyl-5-propyl-4H-1,2,4-triazole

Procedure

2-(1-Adamantyl)-5-propyl-1,3,4-oxadiazole (I) (49 mg, 0.2 mmol) and methylammonium trifluoroacetate (290 mg, 2 mmol, prepared by combining equimolar amounts of methylamine and trifluoroacetic acid in ether followed by concentration in vacuo) were stirred together in a sealed vial at 150° for 18 h. The residue was partitioned with methylene chloride and water, the organic layer washed with 10% K2CO3 and brine. The aqueous phase was extracted with methylene chloride (6×), the combined extracts dried (MgSO4) and concentrated in vacuo. The residue was purified by reverse phase HPLC on a C-18 silica gel column using an acetonitrile-0.1% trifluoroacetic acid gradient to afford 3-(1-adamantyl)-4-methyl-5-propyl-4H-1,2,4-triazole (4-3). MS: 260 (M+1).

Workup

  1. customThe residue was partitioned with methylene chloride and water
  2. washthe organic layer washed with 10% K2CO3 and brine
  3. extractionThe aqueous phase was extracted with methylene chloride (6×)
  4. dry with materialthe combined extracts dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by reverse phase HPLC on a C-18 silica gel column

Sources & evidence

ORD record
ord-2256f4cc61b1406ca9ab772399bd79a0
Source dataset
uspto-grants-2008_02
Patent number
US07329683B2

Reaction notes

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