Methanol → 4''-[3-Butyl-5-oxo-1-(2-trifluoromethyl-phenyl)-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid diphenylacetyl-amide

HRID 36202

Reaktionsgleichung

Reaktionsgleichung von HRID 36202
[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[S:34](=[O:37])(=[O:36])[NH2:35])=[CH:24][CH:23]=2)[C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[N:9]=1)[CH2:2][CH2:3][CH3:4].[C:38]1([CH:44]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:45](Cl)=[O:46])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CO>C(Cl)Cl>[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[S:34](=[O:37])(=[O:36])[NH:35][C:45](=[O:46])[CH:44]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[CH:24][CH:23]=2)[C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 746372,2-Diphenylacetyl chlorideHCID 103469025-n-Butyl-2,4-dihydro-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

Produkt 1

HCID 103727234''-[3-Butyl-5-oxo-1-(2-trifluoromethyl-phenyl)-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid diphenylacetyl-amideAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

By the procedure of Example 13, Step C, 5-n-butyl-2,4-dihydro-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one (from Example 16, Step C) was reacted with diphenylacetyl chloride. The crude product was evaporated twice from toluene and flash chromatographed twice on silica gel (gradient elution with 0.1-1% MeOH in CH2Cl2 and then approx. 0.01-1% MeOH in CH2Cl2) to give a 73% yield of the title compound as off-white crystals, mp 144°-146° C.; homogeneous by TLC in 19:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 725 (M+1)+.

Aufarbeitung

  1. customThe crude product was evaporated twice from toluene and flash
  2. customchromatographed twice on silica gel (
  3. washgradient elution with 0.1-1% MeOH in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-b11e232fa3b849c3bd92a6ef3d5bd793
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411980

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