[2'-(N-t-Butylsulfamoyl)biphenyl-4-yl]methyl bromide → 5-n-butyl-4-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]-2,4-dihydro-2-[4-nitro-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one
Reaction equation
[CH2:1]([C:5]1[NH:6][C:7](=[O:23])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=2[C:19]([F:22])([F:21])[F:20])[N:9]=1)[CH2:2][CH2:3][CH3:4].[C:24]([NH:28][S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38]1[CH:43]=[CH:42][C:41]([CH2:44]Br)=[CH:40][CH:39]=1)(=[O:31])=[O:30])([CH3:27])([CH3:26])[CH3:25]>>[CH2:1]([C:5]1[N:6]([CH2:44][C:41]2[CH:42]=[CH:43][C:38]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[S:29](=[O:31])(=[O:30])[NH:28][C:24]([CH3:25])([CH3:27])[CH3:26])=[CH:39][CH:40]=2)[C:7](=[O:23])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=2[C:19]([F:21])([F:22])[F:20])[N:9]=1)[CH2:2][CH2:3][CH3:4]Participants
3
Reactant 2
Product 1
Procedure
By the procedure of Example 13, Step A, 5-n-butyl-2,4-dihydro-2-[4-nitro-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one (from Step A) was alkylated with [2'-(N-t-butylsulfamoyl)biphenyl-4-yl]-methyl bromide (from Example 12, Step D). Flash chromatography of the crude product on silica gel (gradient elution with 0.5-5.0% MeOH in CH2Cl2) gave an 88% yield of the title compound as an orange solid, mp >78° C. (gradual), homogeneous by TLC (98:2 CH2Cl2 --MeOH), mass spectrum (FAB) m/e 632 (M+1)+.
Sources & evidence
- ORD record
- ord-356755a712cb41e98149b13356b1877c
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05411980
Reaction notes
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