2-Chlorobenzoic Acid → 2-[5-(Acetylamino)-2-chlorophenyl]-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)-sulfamoyl]-3-fluoro-5'-n-propylbiphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 36296Notes

Reaction equation

HRID 36296 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([Cl:42])=[C:9]([N:11]2[C:15](=[O:16])[N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[C:28]([CH2:30][CH2:31][CH3:32])[CH:27]=[CH:26][C:25]=4[S:33](=[O:36])(=[O:35])[NH2:34])=[CH:20][C:19]=3[F:37])[C:13]([CH2:38][CH2:39][CH2:40][CH3:41])=[N:12]2)[CH:10]=1)(=[O:3])[CH3:2].[Cl:43][C:44]1[CH:52]=[CH:51][CH:50]=[CH:49][C:45]=1[C:46](O)=[O:47].C1N=CN(C(N2C=NC=C2)=O)C=1.C1CCN2C(=NCCC2)CC1>>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([Cl:42])=[C:9]([N:11]2[C:15](=[O:16])[N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[C:28]([CH2:30][CH2:31][CH3:32])[CH:27]=[CH:26][C:25]=4[S:33](=[O:36])(=[O:35])[NH:34][C:46](=[O:47])[C:45]4[CH:49]=[CH:50][CH:51]=[CH:52][C:44]=4[Cl:43])=[CH:20][C:19]=3[F:37])[C:13]([CH2:38][CH2:39][CH2:40][CH3:41])=[N:12]2)[CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 83742-Chlorobenzoic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 19939471HCID 19939471, compound

Product 1

HCID 100788002-[5-(Acetylamino)-2-chlorophenyl]-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)-sulfamoyl]-3-fluoro-5'-n-propylbiphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 56%

Procedure

Reaction of 2-[5-(acetylamino)-2-chlorophenyl]-5-n-butyl-2,4-dihydro-4-[(3-fluoro-5'-n-propyl-2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one (from Step E) with 2-chlorobenzoic acid (2 equivalents), CDI (2 equiv), and DBU (2 equiv) according to the procedure of Example 69 gave a 56% yield of the title compound as a white, glassy solid, mp 144°-146° C.; homogeneous by TLC (95:5 CH2Cl2 --MeOH); mass spectrum (FAB) m/e 752 (M+1)+.

Sources & evidence

ORD record
ord-e7b666d145f24557bca2ca0b401c377a
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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