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 220641Notes

Reaction equation

HRID 220641 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C@@H:14](O)[C:15]([F:18])([F:17])[F:16])[C:11](=[O:20])[N:10]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[N:9]=2)=[CH:4][CH:3]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12](/[CH:13]=[CH:14]/[C:15]([F:18])([F:16])[F:17])[C:11](=[O:20])[N:10]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[N:9]=2)=[CH:4][CH:3]=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

280 mg (0.74 mmol) of the compound from Example 7A were introduced at RT together with 108.1 mg (0.89 mmol) of 4-dimethylaminopyridine in 5.3 ml of pyridine, admixed with portions of 0.31 ml (1.84 mmol) of trifluoromethanesulphonic anhydride and stirred for 12 h. The pyridine was removed on a rotary evaporator and the residue was taken up in acetonitrile and 1N hydrochloric acid. The product was purified by preparative HPLC (Method 10). This gave 230 mg (86% of theory) of the title compound.

Workup

  1. customThe pyridine was removed on a rotary evaporator
  2. customThe product was purified by preparative HPLC (Method 10)

Sources & evidence

ORD record
ord-1ede757dfb8342799ac99202aa999569
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

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