Sodium hydride → 2-(2-Chlorophenyl)-2,4-dihydro-5-(3-methylbutyl)-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[NH:11][C:10]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[N:9]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+]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[N:11]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]3[N:39]([C:40]([C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)([C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=4)[C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[N:38]=[N:37][N:36]=3)=[CH:27][CH:28]=2)[C:10]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[N:9]1Participants
4
Reactant 3
Product 1
Procedure
The alkylation of 2-(2-chlorophenyl)-2,4-dihydro-5-(3-methylbutyl)-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 50% excess of the alkylating agent were used. After work-up, the crude product mixture was flash chromatographed on silica gel (72 mL for 0.354 mmol, eluted with 0.3% MeOH/CH2Cl2) to give a 39% yield of the desired material, mass spectrum (FAB) m/e 742 (M+1)+.
Workup
- customchromatographed on silica gel (72 mL for 0.354 mmol, eluted with 0.3% MeOH/CH2Cl2)
Sources & evidence
- ORD record
- ord-51c38cd8e53a4fbd9e4b091f2bc6b4ca
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05411980
Reaction notes
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