Propionyl bromide → 5-n-Butyl-2-[2-chloro-5-(propionylamino)phenyl]-2,4-dihydro-4-[[2'-[N-(2-phenoxybenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one

HRID 36273

Reaktionsgleichung

Reaktionsgleichung von HRID 36273
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:50])=[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:45])(=[O:44])[NH:28][C:29](=[O:43])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[O:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:17][CH:16]=3)[C:10]([CH2:46][CH2:47][CH2:48][CH3:49])=[N:9]2)[CH:7]=1.[C:51](Br)(=[O:54])[CH2:52][CH3:53]>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[CH2:46]([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:45])(=[O:44])[NH:28][C:29](=[O:43])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[CH:19][CH:20]=2)[C:12](=[O:13])[N:8]([C:6]2[CH:7]=[C:2]([NH:1][C:51](=[O:54])[CH2:52][CH3:53])[CH:3]=[CH:4][C:5]=2[Cl:50])[N:9]=1)[CH2:47][CH2:48][CH3:49]

Komponenten

5

Edukt 2

HCID 69018Propionyl bromideHCID 199393842-[5-amino-2-chlorophenyl]-5-n-butyl-2,4-dihydro-4-[[2'-[N-(2-phenoxybenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one

Produkt 1

HCID 199393915-n-Butyl-2-[2-chloro-5-(propionylamino)phenyl]-2,4-dihydro-4-[[2'-[N-(2-phenoxybenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-oneAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

By the procedure of Example 69, 2-[5-amino-2-chlorophenyl]-5-n-butyl-2,4-dihydro-4-[[2'-[N-(2-phenoxybenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one (from Step B) was reacted with propionyl bromide in the presence of DMAP. The crude product was reconcentrated from toluene and flash chromatographed on silica gel (gradient elution with 1-2% MeOH in CH2Cl2) to give a 65% yield of the title compound as a stiff foam, mp 113°-116° C.; homogeneous by TLC in 9:1 CH2Cl2 ; mass spectrum (FAB) m/e 764 (M+1)+.

Aufarbeitung

  1. customchromatographed on silica gel (gradient elution with 1-2% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-cbf438c3663646cc9cb4da676df9d912
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411980

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