Methyl 4-(bromomethyl)benzoate → 5-n-Butyl-2,4-dihydro-4-[4-(methoxycarbonyl)benzyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

HRID 36205Notes

Reaction equation

HRID 36205 reaction equation
[CH2:1]([C:5]1[NH:6][C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[N:9]=1)[CH2:2][CH2:3][CH3:4].Br[CH2:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1>>[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:31][CH:32]=2)[C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 1355270275-n-Butyl-2,4-dihydro-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

Product 1

HCID 199394365-n-Butyl-2,4-dihydro-4-[4-(methoxycarbonyl)benzyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-oneYield 53%

Procedure

Alkylation of 5-n-butyl-2,4-dihydro-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one (from Example 16, Step A) with methyl 4-(bromomethyl)benzoate was carried out according to the procedure of Example 13, Step A. Purification of the crude product by flash chromatography on silica gel (gradient elution with 0.3-1% MeOH in CH2Cl2) provided a 53% yield of the title compound as a clear, glassy solid; homogeneous by TLC in 95:5 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 434 (M+1)+.

Workup

  1. customPurification of the crude product by flash chromatography on silica gel (gradient elution with 0.3-1% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-9f8e5f3a6c86435ab3415d2198bd9473
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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