4'-(Bromomethyl)-N-t-butyl-3'-fluoro-2-biphenylsulfonamide → 2-(2-Bromo-5-nitrophenyl)-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 36299Notes

Reaction equation

HRID 36299 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[NH:14][C:13]([CH2:17][CH2:18][CH2:19][CH3:20])=[N:12]1.[F:21][C:22]1[CH:23]=[C:24]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[S:36](=[O:43])(=[O:42])[NH:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH:25]=[CH:26][C:27]=1[CH2:28]Br>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[N:14]([CH2:28][C:27]2[CH:26]=[CH:25][C:24]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[S:36](=[O:42])(=[O:43])[NH:37][C:38]([CH3:41])([CH3:39])[CH3:40])=[CH:23][C:22]=2[F:21])[C:13]([CH2:17][CH2:18][CH2:19][CH3:20])=[N:12]1

Participants

3

Reactant 2

HCID 100465214'-(Bromomethyl)-N-t-butyl-3'-fluoro-2-biphenylsulfonamideHCID 1357200802-(2-Bromo-5-nitrophenyl)-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 103494052-(2-Bromo-5-nitrophenyl)-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 93%

Procedure

The alkylation of 2-(2-bromo-5-nitrophenyl)-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one (from Example 75, Step A) with [3-fluoro-2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl bromide (from Step B) was carried out according to the procedure of Example 13, Step A, to give a 93% yield of the title compound as a brownish, stiff foam, mp 137°-139° C., homogeneous by TLC in 98:2 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 666, 668 (M+Li)+.

Sources & evidence

ORD record
ord-fff714aea1db4742a85577f91477627b
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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