5-[4'-(Azidomethyl)[1,1'-biphenyl]-2-yl]-1-(triphenylmethyl)-1H-tetrazole → 2,4-Bis[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 36223Notes

Reaction equation

HRID 36223 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]3[N:28]([C:29]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:27]=[N:26][N:25]=3)=[CH:14][CH:13]=2)[C:7](=[O:10])[NH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].N([CH2:51][C:52]1[CH:57]=[CH:56][C:55]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=2[C:64]2[N:68]([C:69]([C:82]3[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=3)([C:76]3[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=3)[C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=3)[N:67]=[N:66][N:65]=2)=[CH:54][CH:53]=1)=[N+]=[N-]>>[C:69]([N:68]1[C:64]([C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][C:58]=2[C:55]2[CH:54]=[CH:53][C:52]([CH2:51][N:8]3[C:7](=[O:10])[N:6]([CH2:11][C:12]4[CH:13]=[CH:14][C:15]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=5[C:24]5[N:28]([C:29]([C:36]6[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=6)([C:30]6[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=6)[C:42]6[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=6)[N:27]=[N:26][N:25]=5)=[CH:16][CH:17]=4)[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:9]3)=[CH:57][CH:56]=2)=[N:65][N:66]=[N:67]1)([C:82]1[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=1)([C:70]1[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=1)[C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1

Participants

3

Reactant 2

HCID 149873355-[4'-(Azidomethyl)[1,1'-biphenyl]-2-yl]-1-(triphenylmethyl)-1H-tetrazoleHCID 199393865-n-Butyl-2,4-dihydro-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one

Product 1

HCID 199394702,4-Bis[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 96%

Procedure

The alkylation of 5-n-butyl-2,4-dihydro-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one (from Example 2, Step D) with 5-[4'-(bromomethyl)-biphenyl-2-yl]-N-trityltetrazole (see Example 2, Step B) was carried out as described in Example 3, Step A, except that only 3 equivalents of the alkylating agent was used. After work-up, the residue was flash chromatographed over silica gel (25 mL for 0.162 mmole, gradient elution using 0.25-1.0% MeOH/CH2Cl2) to give the desired material as a white foam in 96% yield, homogeneous by TLC in 2% MeOH/CH2Cl2, mass spectrum (FAB) 1094 (M+1)+.

Workup

  1. customchromatographed over silica gel (25 mL for 0.162 mmole, gradient elution using 0.25-1.0% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-8370d2d16d814d9a81fae62db1cb4f90
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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