(1-Bromopropyl)benzene → 5-n-Butyl-2,4-dihydro-2-(1-phenylpropyl)-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one
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].Br[CH:49]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[CH2:50][CH3:51]>>[CH2:1]([C:5]1[N:6]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[N:28]([C:29]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[N:27]=[N:26][N:25]=3)=[CH:16][CH:17]=2)[C:7](=[O:10])[N:8]([CH:49]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH2:50][CH3:51])[N:9]=1)[CH2:2][CH2:3][CH3:4]Participants
3
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 1-bromo-1-phenylpropane was carried out as described in Example 3, Step A. After work-up, the residue was flash chromatographed over silica gel (gradient elution using 0.2-1.0% MeOH/CH2Cl2) to give the desired material in 50% yield, homogeneous by TLC in 2% MeOH/CH2Cl2, mass spectrum (FAB) 736 (M+1)+.
Workup
- customchromatographed over silica gel (gradient elution using 0.2-1.0% MeOH/CH2Cl2)
Sources & evidence
- ORD record
- ord-61fa9412ce6a4a6b9efa48a5dd6cdbb9
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05411980
Reaction notes
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