Dichloromethane → 5-n-Butyl-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-2-[5-(propionylamino)-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

HRID 36305

Reaktionsgleichung

Reaktionsgleichung von HRID 36305
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:40]([F:43])([F:42])[F:41])=[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:34])(=[O:33])[NH:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:17][C:16]=3[F:35])[C:10]([CH2:36][CH2:37][CH2:38][CH3:39])=[N:9]2)[CH:7]=1.[C:44](Br)(=[O:47])[CH2:45][CH3:46].C(Cl)Cl>CN(C1C=CN=CC=1)C.CO>[CH2:36]([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:33])(=[O:34])[NH:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[CH:17][C:16]=2[F:35])[C:12](=[O:13])[N:8]([C:6]2[CH:7]=[C:2]([NH:1][C:44](=[O:47])[CH2:45][CH3:46])[CH:3]=[CH:4][C:5]=2[C:40]([F:42])([F:41])[F:43])[N:9]=1)[CH2:37][CH2:38][CH3:39]

Komponenten

6

Edukt 3

HCID 6344DichloromethaneHCID 69018Propionyl bromideHCID 117585652-[5-Amino-2-(trifluoromethyl)phenyl]-5-n-butyl-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Produkt 1

HCID 199394055-n-Butyl-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-2-[5-(propionylamino)-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

The title compound was prepared by reaction of 2-[5-amino-2-(trifluoromethyl)phenyl]-5-n-butyl-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step A) with propionyl bromide (3 equivalents) in the presence of DMAP (1.1 equiv) following the method of Example 69. Chromatographic purification of the crude product on silica gel (elution with 0.8% MeOH in CH2Cl2) afforded a nearly quantitative yield of off-white, stiff foam; homogeneous by TLC in 95:5 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 682 (M+Li)+.

Aufarbeitung

  1. customChromatographic purification of the crude product on silica gel (elution with 0.8% MeOH in CH2Cl2)
  2. customafforded a nearly quantitative yield of off-white, stiff foam

Quellen und Nachweise

ORD-Eintrag
ord-c7ecbf3c93d54e918103509d13bb3b8b
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411980

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