1,2-Dichloroethane → 2-(2-Chlorophenyl)-3-[({3-(4-chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetyl)amino]propyl carbamate

HRID 709164Notes

Reaction equation

HRID 709164 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12](/[CH:13]=[CH:14]/[C:15]([F:18])([F:17])[F:16])[C:11](=[O:19])[N:10]([CH2:20][C:21](O)=[O:22])[N:9]=2)=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:38](=[O:52])([O:40][CH2:41][CH:42]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[Cl:51])[CH2:43][NH2:44])[NH2:39]>CN(C=O)C>[C:38](=[O:52])([O:40][CH2:41][CH:42]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[Cl:51])[CH2:43][NH:44][C:21](=[O:22])[CH2:20][N:10]1[C:11](=[O:19])[N:12](/[CH:13]=[CH:14]/[C:15]([F:18])([F:17])[F:16])[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[N:9]1)[NH2:39]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 59536906{3-(4-Chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetic acidHCID 680324153-Amino-2-(2-chlorophenyl)propyl carbamate

Product 1

HCID 666356562-(2-Chlorophenyl)-3-[({3-(4-chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetyl)amino]propyl carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 47 mg (135 μmol) of the compound of Example 33A, 34 mg (176 μmol) of EDC and 24 mg (176 μmol) of HOBt in 1 ml of DMF was stirred at RT for 1 h, and 34 mg (149 μmol) of the compound of Example 15A were then added. The mixture was stirred at RT for 16 h and then separated directly by preparative HPLC [Method 9] into its components. This gave 28 mg (37% of theory) of the title compound.

Workup

  1. stirringThe mixture was stirred at RT for 16 h
  2. customseparated directly by preparative HPLC [Method 9] into its components

Sources & evidence

ORD record
ord-54c8e85e9202484b800f5ada1f05d262
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

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