Sodium hydride → 5-n-Butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2-[2-chloro-5-(valerylamino)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 36253

Reaction equation

HRID 36253 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:44])=[C:6]([N:8]2[C:12](=[O:13])[N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[S:27](=[O:39])(=[O:38])[NH:28][C:29](=[O:37])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[Cl:36])=[CH:17][CH:16]=3)[C:10]([CH2:40][CH2:41][CH2:42][CH3:43])=[N:9]2)[CH:7]=1.[H-].[Na+].[C:47](Cl)(=[O:52])[CH2:48][CH2:49][CH2:50][CH3:51]>>[CH2:40]([C:10]1[N:11]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27](=[O:38])(=[O:39])[NH:28][C:29](=[O:37])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])=[CH:19][CH:20]=2)[C:12](=[O:13])[N:8]([C:6]2[CH:7]=[C:2]([NH:1][C:47](=[O:52])[CH2:48][CH2:49][CH2:50][CH3:51])[CH:3]=[CH:4][C:5]=2[Cl:44])[N:9]=1)[CH2:41][CH2:42][CH3:43]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 61186Valeryl chlorideHCID 100321934''-[1-(5-Amino-2-chloro-phenyl)-3-butyl-5-oxo-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid 2-chloro-benzoylamide

Product 1

HCID 100786635-n-Butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2-[2-chloro-5-(valerylamino)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Procedure

The title compound was prepared from 2-(5-amino-2-chlorophenyl)-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Example 60), sodium hydride, and valeryl chloride according the procedure of Example 57. The crude product was flash chromatographed over silica gel (gradient elution with 0.5-2.0% MeOH/CH2Cl2) to give the desired compound as a cream-colored solid in 48% yield, mp >110° C. (gradual), homogeneous by TLC (9:1 MeOH/CH2Cl2), mass spectrum (FAB) m/e 734 (M+1)+.

Workup

  1. customchromatographed over silica gel (gradient elution with 0.5-2.0% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-e3472501156347b7b2f8f4a608c55708
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Linked notes

Loading…