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

Reaction equation

HRID 36305 reaction equation
[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]

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-c7ecbf3c93d54e918103509d13bb3b8b
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Linked notes

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