1,2-Dichloroethane → 2-[3-(4-chlorophenyl)-4-(2-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-[2-(2-trifluoromethyl-phenyl)ethyl]-acetamide

HRID 660941Notes

Reaction equation

HRID 660941 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.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[F:40][C:41]([F:52])([F:51])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[CH2:48][CH2:49][NH2:50]>CN(C=O)C>[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]([NH:50][CH2:49][CH2:48][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=3[C:41]([F:40])([F:51])[F:52])=[O:24])[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 698832-(Trifluoromethyl)phenethylamineHCID 757711-HydroxybenzotriazoleHCID 58012119[3-(4-chlorophenyl)-4-(2-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acid

Product 1

HCID 580120112-[3-(4-chlorophenyl)-4-(2-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-[2-(2-trifluoromethyl-phenyl)ethyl]-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The carboxylic acid from Example 156A (60 mg, 0.14 mmol) and HOBt (27.0 mg, 0.20 mmol) are placed in 0.86 ml DMF and treated at RT with 38.2 mg (0.20 mmol) of EDC. After 20 mins, 27 mg of 2-(2-trifluoromethyl-phenyl)ethylamine (0.14 mmol) are added and the mixture is stirred overnight at RT. The mixture is then directly separated by preparative HPLC (Method 20). 69 mg (91% of theory) of the title compound are obtained.

Workup

  1. customThe mixture is then directly separated by preparative HPLC (Method 20)

Sources & evidence

ORD record
ord-6f3b84f8678e485cb001d9233a1dbaad
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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