Trifluoromethanesulfonic anhydride → Methyl {3-(4-chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetate

HRID 574141Notes

Reaction equation

HRID 574141 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][N:5]1[C:9](=[O:10])[N:8]([CH2:11][C@@H:12](O)[C:13]([F:16])([F:15])[F:14])[C:7]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[N:6]1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:25])[CH2:4][N:5]1[C:9](=[O:10])[N:8](/[CH:11]=[CH:12]/[C:13]([F:16])([F:15])[F:14])[C:7]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)=[N:6]1

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 59536753Methyl {3-(4-chlorophenyl)-5-oxo-4-[(2R)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetate

Product 1

HCID 59536880Methyl {3-(4-chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

At RT, 280 mg (0.74 mmol) of the compound of Example 7A were initially charged together with 108 mg (0.89 mmol) of 4-dimethylaminopyridine in 5.3 ml of pyridine, 0.31 ml of trifluoromethanesulphonic anhydride (1.84 mmol) was added in portions and the mixture was stirred for 12 h. The pyridine was removed on a rotary evaporator. The residue was taken up in acetonitrile and 1N hydrochloric acid and purified by preparative HLPC [Method 9]. This gave 230 mg (86% of theory) of the title compound.

Workup

  1. additionwas added in portions
  2. customThe pyridine was removed on a rotary evaporator
  3. custom1N hydrochloric acid and purified by preparative HLPC [Method 9]

Sources & evidence

ORD record
ord-6489ad2aef9c4eb98cdb21e16d3945ac
Source dataset
uspto-grants-2015_05
Patent number
US09034855B2

Reaction notes

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