Sodium hydride → 5-n-Butyl-2,4-dihydro-2-[1-(carbomethoxy)ethyl]-4-[(2'-cyanobiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one

HRID 36217

Reaction equation

HRID 36217 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]#[N:25])=[CH:14][CH:13]=2)[C:7](=[O:10])[NH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].Br[CH:27]([CH3:32])[C:28]([O:30][CH3:31])=[O:29].[H-].[Na+]>>[CH2:1]([C:5]1[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]#[N:25])=[CH:14][CH:13]=2)[C:7](=[O:10])[N:8]([CH:27]([C:28]([O:30][CH3:31])=[O:29])[CH3:32])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 95576Methyl 2-bromopropionateHCID 149510524'-[(3-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)methyl]biphenyl-2-carbonitrile

Product 1

HCID 149568225-n-Butyl-2,4-dihydro-2-[1-(carbomethoxy)ethyl]-4-[(2'-cyanobiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-oneYield 84%

Procedure

The alkylation of 5-n-butyl-4-[(2'-cyanobiphenyl-4-yl)methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (from Example 9, Step C) with methyl 2-bromopropionate was carried out as described in Example 3, Step A, except that no excess sodium hydride was used. After work-up, the residue was flash chromatographed over silica gel (eluted with 0.5% MeOH/CH2Cl2) to give the desired material in 84% yield as a colorless oil, homogeneous by TLC in 2% MeOH/CH2Cl2, mass spectrum (FAB) 419 (M+1)+.

Workup

  1. customchromatographed over silica gel (eluted with 0.5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-d15377aa467143e7984753cb26e63cb6
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Linked notes

Loading…