1,2-Dichloroethane → 2-({[3-(4-Chlorophenyl)-4-(2-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetyl}-amino)-1-[2-(trifluoromethyl)phenyl]ethyl carbamate

HRID 709162Notes

Reaction equation

HRID 709162 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:42])([O:28][CH:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38]([F:41])([F:40])[F:39])[CH2:30][NH2:31])[NH2:27].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl>CN(C=O)C>[C:26](=[O:42])([O:28][CH:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38]([F:41])([F:40])[F:39])[CH2:30][NH:31][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

7

Reactant 5

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 58012119[3-(4-chlorophenyl)-4-(2-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acidHCID 666356272-Amino-1-[2-(trifluoromethyl)phenyl]ethyl carbamate

Product 1

HCID 666349642-({[3-(4-Chlorophenyl)-4-(2-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetyl}-amino)-1-[2-(trifluoromethyl)phenyl]ethyl carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 40 mg (111 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], 33 mg (133 μmol) of the compound of Example 37A, 25 mg (133 μmol) of EDC and 21 mg (133 μmol) of HOBt in 2.4 ml of DMF was stirred at RT overnight, 1 ml of 1 M hydrochloric acid was then added and the mixture was separated directly by preparative HPLC [Method 20] into its components. This gave 53 mg (81% of theory) of the title compound.

Workup

  1. customthe mixture was separated directly by preparative HPLC [Method 20] into its components

Sources & evidence

ORD record
ord-9f8156dc8a244651b6b71d31edabf75c
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

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