Sodium hydride → HCID 10484866, compound

HRID 36264Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.[H-].[Na+].[C:46](Cl)(=[O:51])[CH2:47][CH2:48][CH2:49][CH3:50]>>[CH2:40]([C:10]1[N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27](=[O:39])(=[O:38])[NH:28][C:29](=[O:37])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])=[CH:17][CH:16]=2)[C:12](=[O:13])[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:46](=[O:51])[CH2:47][CH2:48][CH2:49][CH3:50])[CH:3]=2)[N:9]=1)[CH2:41][CH2:42][CH3:43]

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 61186Valeryl chloride

HCID 100089622-(3-aminophenyl)-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 10484866HCID 10484866, compoundYield 67%

Procedure

This material was prepared from 2-(3-aminophenyl)-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 66, Step E), sodium hydride, and valeryl chloride according to the procedure of Example 62. The crude product was flash chromatographed over silica gel to afford the title compound in 67% yield as a cream-colored solid, mp 102°-105° C., homogeneous by TLC (9:1 MeOH/CH2Cl2), mass spectrum (FAB) m/e 700 (M+1)+.

Workup

customchromatographed over silica gel

Sources & evidence

ORD record: ord-e7e73abdfff54cb4bf9ef1ba43fbe68c
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05411980

Reaction notes

Loading…