[3-(4-chlorophenyl)-4-(2-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acid → 2-(2-Chlorophenyl)-3-({[3-(4-chlorophenyl)-4-(2-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetyl}amino)propyl carbamate

HRID 709165Notes

Reaction equation

HRID 709165 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:11](=[O:21])[N:10]([CH2:22][C:23](O)=[O:24])[N:9]=2)=[CH:4][CH:3]=1.[C:26](=[O:40])([O:28][CH2:29][CH:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[Cl:39])[CH2:31][NH2:32])[NH2:27]>>[C:26](=[O:40])([O:28][CH2:29][CH:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[Cl:39])[CH2:31][NH:32][C:23](=[O:24])[CH2:22][N:10]1[C:11](=[O:21])[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[N:9]1)[NH2:27]

Participants

3

Reactant 2

HCID 58012119[3-(4-chlorophenyl)-4-(2-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acidHCID 680324153-Amino-2-(2-chlorophenyl)propyl carbamate

Product 1

HCID 666355512-(2-Chlorophenyl)-3-({[3-(4-chlorophenyl)-4-(2-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetyl}amino)propyl carbamate

Procedure

Analogously to the procedure of Example 63, 49 mg (135 μmol) of [3-(4-chlorophenyl)-4-(2-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acid [for the preparation see Example 156A in WO 2007/134862] were reacted with 34 mg (149 μmol) of the compound of Example 15A. This gave 27 mg (35% of theory) of the title compound.

Sources & evidence

ORD record
ord-7ffb5bacabef4b429e1e62aec9b41932
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

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