Sodium hydride → 5-Cyclopropyl-2,4-dihydro-2-(2-nitrophenyl)-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one

HRID 36232Notes

Reaction equation

HRID 36232 reaction equation
[CH:1]1([C:4]2[NH:5][C:6](=[O:18])[N:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N+:15]([O-:17])=[O:16])[N:8]=2)[CH2:3][CH2:2]1.N([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]2[N:39]([C:40]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[N:38]=[N:37][N:36]=2)=[CH:25][CH:24]=1)=[N+]=[N-].[H-].[Na+]>>[CH:1]1([C:4]2[N:5]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[C:35]4[N:39]([C:40]([C:53]5[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=5)([C:47]5[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=5)[C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)[N:38]=[N:37][N:36]=4)=[CH:27][CH:28]=3)[C:6](=[O:18])[N:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N+:15]([O-:17])=[O:16])[N:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 149873355-[4'-(Azidomethyl)[1,1'-biphenyl]-2-yl]-1-(triphenylmethyl)-1H-tetrazoleHCID 1357200845-Cyclopropyl-2,4-dihydro-2-(2-nitrophenyl)-3H-1,2,4-triazol-3-one

Product 1

HCID 199395105-Cyclopropyl-2,4-dihydro-2-(2-nitrophenyl)-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-oneYield 59%

Procedure

The alkylation of 5-cyclopropyl-2,4-dihydro-2-(2-nitrophenyl)-3H-1,2,4-triazol-3-one with 5-[4'-bromomethyl)biphenyl-2-yl]-N-trityltetrazole (see Example 2, Step B) was carried out as described in Example 4, Step D, except that a 20% excess of sodium hydride and 20% excess of the alkylating agent were used. After work-up, the crude product mixture was flash chromatographed on silica gel (124 mL for 0.467 mmole, eluted with 0.5% MeOH/CH2Cl2) to give a 59% yield of the desired material as a yellow foam, homogeneous by TLC in 2% MeOH/CH2Cl2, mass spectrum (FAB) m/e 723 (M+1)+.

Workup

  1. customchromatographed on silica gel (124 mL for 0.467 mmole, eluted with 0.5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-472c1dcd9a58400c980c907d8ea6ef1d
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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