Dichloromethane → 5-n-Butyl-2-[2-chloro-5-(propionylamino)-phenyl]-2,4-dihydro-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one

HRID 1198707Notes

Reaction equation

HRID 1198707 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[S:36](=[O:43])(=[O:42])[NH:37]C(C)(C)C)=[CH:26][C:25]=2[F:44])[C:7](=[O:22])[N:8]([C:10]2[CH:15]=[C:14]([NH:16][C:17](=[O:20])[CH2:18][CH3:19])[CH:13]=[CH:12][C:11]=2[Cl:21])[N:9]=1)[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.C(Cl)Cl>CO>[CH2:1]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[S:36](=[O:42])(=[O:43])[NH2:37])=[CH:26][C:25]=2[F:44])[C:7](=[O:22])[N:8]([C:10]2[CH:15]=[C:14]([NH:16][C:17](=[O:20])[CH2:18][CH3:19])[CH:13]=[CH:12][C:11]=2[Cl:21])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 104391465-n-Butyl-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-2-[2-chloro-5-(propionylamino)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 103483205-n-Butyl-2-[2-chloro-5-(propionylamino)-phenyl]-2,4-dihydro-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-oneYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared in 90% yield by deprotection of 5-n-butyl-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-2-[2-chloro-5-(propionylamino)-phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step D) with trifluoroacetic acid in the presence of anisole according to the procedure of Example 28, Step G. The material was obtained as a white solid, mp 135°-137° C.; satisfactory purity by TLC (95:5 CH2Cl2 --MeOH); mass spectrum (FAB) m/e 586 (M+1)+.

Workup

  1. customThe material was obtained as a white solid, mp 135°-137° C.

Sources & evidence

ORD record
ord-7a574f9cdf80425b94ab6006dfdabb7e
Source dataset
uspto-grants-1994_01
Patent number
US05281614

Reaction notes

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