Ethanone, 1-(1-methyl-1H-1,2,4-triazol-3-yl)- (9CI) → HCID 86669574, compound

HRID 1398516Notes

Reaction equation

HRID 1398516 reaction equation
[C:1]([Mg]Br)#[CH:2].[CH3:5][N:6]1[CH:10]=[N:9][C:8]([C:11](=[O:13])[CH3:12])=[N:7]1>C1COCC1>[CH3:5][N:6]1[CH:10]=[N:9][C:8]([C:11]([OH:13])([C:1]#[CH:2])[CH3:12])=[N:7]1

Participants

4

Reactant 2

HCID 14978352Ethanone, 1-(1-methyl-1H-1,2,4-triazol-3-yl)- (9CI)HCID 178418486HCID 178418486, compound

Product 1

HCID 86669574HCID 86669574, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethynylmagnesium bromide (0.5M in THF, 4.32 mL, 2.16 mmol) at 0° C. was added 1-(1-methyl-1,2,4-triazol-3-yl)ethanone (180 mg, 1.44 mmol) in THF (5 mL) slowly. The reaction mixture was allowed to warm to RT and stirred for a further 1.5 hr. The reaction mixture was quenched with saturated aqueous NH4Cl solution (10 mL) and the organics were removed in vacuo. The product was extracted into EtOAc (×2) and the combined organics were dried (Na2SO4), filtered and concentrated in vacuo. Purification by column chromatography eluting with 2-10% methanol in DCM afforded the title compound: 1H NMR (500 MHz, CDCl3) delta 1.93 (3H, s), 2.62 (1H, s), 3.53 (1H, s), 3.93 (3H, s), 8.01 (1H, s); LC-MS: m/z=+152.0 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous NH4Cl solution (10 mL)
  2. customthe organics were removed in vacuo
  3. extractionThe product was extracted into EtOAc (×2)
  4. dry with materialthe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography
  8. washeluting with 2-10% methanol in DCM

Sources & evidence

ORD record
ord-f639fbe3400141b3ae1be4e5018b2df3
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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