5-n-butyl-2-cyclopropyl-4-[(2'-cyanobiphenyl-4-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one → HCID 178441900, compound

HRID 36225

Reaction equation

HRID 36225 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]#[N:28])=[CH:17][CH:16]=2)[C:7](=[O:13])[N:8]([CH:10]2[CH2:12][CH2:11]2)[N:9]=1)[CH2:2][CH2:3][CH3:4].[NH:29]1C=N[N:31]=[N:30]1>C(Cl)Cl>[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:19][CH:20]=2)[C:7](=[O:13])[N:8]([CH:10]2[CH2:12][CH2:11]2)[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 199393755-n-butyl-2-cyclopropyl-4-[(2'-cyanobiphenyl-4-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-oneHCID 178418441HCID 178418441, compound

Product 1

HCID 178441900HCID 178441900, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

The conversion of 5-n-butyl-2-cyclopropyl-4-[(2'-cyanobiphenyl-4-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one to the corresponding tetrazole was accomplished by the procedure of Example 9, Step E, except that it was stirred at 120° C. for 2 days. After work-up, the residue was taken up in CH2Cl2 and flash chromatographed over silica gel (5 mL for 0.091 mmole, gradient elution using 2-10% MeOH/CH2Cl2) to give the desired compound as an oil in 34% yield, homogeneous by TLC in 10% MeOH/CH2Cl2, mass spectrum (FAB) 416 (M+1)+.

Workup

  1. customflash chromatographed over silica gel (5 mL for 0.091 mmole, gradient elution using 2-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-d8397f733daa42ec93ea4fb5f5315441
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Linked notes

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