HCID 19939468, compound → 5-n-Butyl-2-[5-(N-n-butylcarbamoyl)-2-chlorophenyl]-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 1198687Notes

Reaction equation

HRID 1198687 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[S:38](=[O:45])(=[O:44])[NH:39]C(C)(C)C)=[CH:28][C:27]=2[F:46])[C:7](=[O:24])[N:8]([C:10]2[CH:15]=[C:14]([C:16](=[O:22])[NH:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:13]=[CH:12][C:11]=2[Cl:23])[N:9]=1)[CH2:2][CH2:3][CH3:4]>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[CH2:1]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[S:38](=[O:44])(=[O:45])[NH2:39])=[CH:28][C:27]=2[F:46])[C:7](=[O:24])[N:8]([C:10]2[CH:15]=[C:14]([C:16](=[O:22])[NH:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:13]=[CH:12][C:11]=2[Cl:23])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 19939468HCID 19939468, compound

Product 1

HCID 103715965-n-Butyl-2-[5-(N-n-butylcarbamoyl)-2-chlorophenyl]-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 69%

Reagents, catalysts & solvents 2

HCID 7519AnisoleCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 32 mg (0.048 mmol) of 5-n-butyl-2-[5-(N-n-butylcarbamoyl)-2-chlorophenyl]-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step F) in 0.5 mL of trifluoroacetic acid (TFA) containing 2 drops of anisole was stirred overnight at room temperature. The excess TFA was removed by evaporation under a gentle stream of N2. The residue was reconcentrated from toluene twice in vacuo and flash chromatographed over 15 cc of silica gel (gradient elution with 0.5-2% MeOH in CH2Cl2) to give 20 mg (69%) of the title compound as a white solid, mp 108°-110° C.; homogeneous by TLC (95:5 CH2Cl2 --MeOH); mass spectrum (FAB) m/e 614 (M+1)+.

Workup

  1. customThe excess TFA was removed by evaporation under a gentle stream of N2
  2. customchromatographed over 15 cc of silica gel (gradient elution with 0.5-2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-0d081283e97448dbb0e7d9036bccf0ec
Source dataset
uspto-grants-1994_01
Patent number
US05281614

Reaction notes

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