Propionyl bromide → N-[2-[4-[[3-butyl-5-oxo-1-[5-(propanoylamino)-2-(trifluoromethyl)phenyl]-1,2,4-triazol-4-yl]methyl]-3-fluorophenyl]phenyl]sulfonyl-2-chlorobenzamide

HRID 36303

Reaction equation

HRID 36303 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:45]([F:48])([F:47])[F:46])=[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: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][C:16]=3[F:40])[C:10]([CH2:41][CH2:42][CH2:43][CH3:44])=[N:9]2)[CH:7]=1.[C:49](Br)(=[O:52])[CH2:50][CH3:51].C1CCN2C(=NCCC2)CC1>C(Cl)Cl.CO>[CH2:41]([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:38])(=[O:39])[NH:28][C:29](=[O:37])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])=[CH:17][C:16]=2[F:40])[C:12](=[O:13])[N:8]([C:6]2[CH:7]=[C:2]([NH:1][C:49](=[O:52])[CH2:50][CH3:51])[CH:3]=[CH:4][C:5]=2[C:45]([F:46])([F:47])[F:48])[N:9]=1)[CH2:42][CH2:43][CH3:44]

Participants

5

Reactant 3

HCID 69018Propionyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199394462-[5-amino-2-(trifluoromethyl)phenyl]-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 10395335N-[2-[4-[[3-butyl-5-oxo-1-[5-(propanoylamino)-2-(trifluoromethyl)phenyl]-1,2,4-triazol-4-yl]methyl]-3-fluorophenyl]phenyl]sulfonyl-2-chlorobenzamideYield 60%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was synthesized by reaction of 2-[5-amino-2-(trifluoromethyl)phenyl]-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step G) with propionyl bromide (3 equivalents) and DBU (1.1 equiv) according to the method of Example 69. The material was obtained in 60% yield as a pale yellow solid, mp 181°-183° C.; homogeneous by TLC in 9:1 CH2Cl2 -MeOH; mass spectrum (FAB) m/e 796 (M+K)+.

Workup

  1. customThe material was obtained in 60% yield as a pale yellow solid, mp 181°-183° C.

Sources & evidence

ORD record
ord-28b94c3178b9471c9dca3e858d554c9e
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Linked notes

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