Reaktion #64584

ord-0857376cb8d44a71bf1bd924fb40b46d

Reaktionsgleichung

CCCCc1nn(-c2cc(NC(=O)CC)ccc2C(F)(F)F)c(=O)n1Cc1ccc(-c2ccccc2S(N)(=O)=O)cc1F
5-n-butyl-2,4-dihydro-4-[(3-fluoro-2'-sulfamoyl-biphenyl-4-yl)methyl]-2-[5-(propionylamino)-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one
O=C(O)c1ccccc1F
2-fluorobenzoic acid
O=C(n1ccnc1)n1ccnc1
CDI
C1CCC2=NCCCN2CC1
DBU
→
CCCCc1nn(-c2cc(NC(=O)CC)ccc2C(F)(F)F)c(=O)n1Cc1ccc(-c2ccccc2S(=O)(=O)NC(=O)c2ccccc2F)cc1F
title compound
Ausbeute 93.0%
CCCCc1nn(-c2cc(NC(=O)CC)ccc2C(F)(F)F)c(=O)n1Cc1ccc(-c2ccccc2S(=O)(=O)NC(=O)c2ccccc2F)cc1F
5-n-Butyl-2,4-dihydro-4-[[3-fluoro-2'-[N-(2-fluorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2-[5-(propionylamino)-2-(trifluoromethyl)phenyl]-3H-1,2,4,-triazol-3-one
Ausbeute 93.0%

Edukte

CCCCc1nn(-c2cc(NC(=O)CC)ccc2C(F)(F)F)c(=O)n1Cc1ccc(-c2ccccc2S(N)(=O)=O)cc1F
5-n-butyl-2,4-dihydro-4-[(3-fluoro-2'-sulfamoyl-biphenyl-4-yl)methyl]-2-[5-(propionylamino)-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one
O=C(O)c1ccccc1F
2-fluorobenzoic acid
O=C(n1ccnc1)n1ccnc1
CDI
C1CCC2=NCCCN2CC1
DBU

Reagenzien

CN(C)c1ccncc1
DMAP

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Reaction of 5-n-butyl-2,4-dihydro-4-[(3-fluoro-2'-sulfamoyl-biphenyl-4-yl)methyl]-2-[5-(propionylamino)-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one (from Step C) with 2-fluorobenzoic acid (3 equivalents), CDI (3 equiv), DBU (3 equiv), and DMAP (3 equiv) according to the method of Example 51 (as modified in Example 81) gave a a 93% yield of the title compound as a white, stiff foam, mp 119°-122° C.; homogeneous by TLC in 9:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 742 (M+1)+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05411980uspto-grants-1995_05