Ethanol → 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

HRID 36304Notes

Reaction equation

HRID 36304 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[S:37](=[O:44])(=[O:43])[NH:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:27][C:26]=2[F:45])[C:7](=[O:23])[N:8]([C:10]2[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:11]=2[C:19]([F:22])([F:21])[F:20])[N:9]=1)[CH2:2][CH2:3][CH3:4].C(O)C>C(OCC)(=O)C>[NH2:16][C:14]1[CH:13]=[CH:12][C:11]([C:19]([F:20])([F:22])[F:21])=[C:10]([N:8]2[C:7](=[O:23])[N:6]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[S:37](=[O:43])(=[O:44])[NH:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[CH:27][C:26]=3[F:45])[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:9]2)[CH:15]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 117648385-n-Butyl-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-2-[5-nitro-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

Product 1

HCID 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-oneYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Hydrogenation of 5-n-butyl-4-[[2'-(N-t-butylsulfamoyl)-3-fluoro-biphenyl-4-yl]methyl]-2,4-dihydro-2-[5-nitro-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one (from Example 84, Step D) was carried out according to the procedure of Example 75, Step D, except that a 4:1 ratio of ethanol and ethyl acetate was used as solvent. The title compound was obtained in 91% yield oas an off-white foam, suitable for use without further purification; nearly homogeneous by TLC in 95:5 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 626 (M+Li)+.

Sources & evidence

ORD record
ord-1941268571b640449e5f56ae360f39e1
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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