1,2-Dichloroethane → 2-[3-(4-Chlorophenyl)-5-oxo-4-(3,3,3-trifluoropropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-{1-(2,3-dichlorophenyl)-2-[(ethylcarbamoyl)amino]ethyl}acetamide

HRID 220708Notes

Reaction equation

HRID 220708 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:11](=[O:19])[N:10]([CH2:20][C:21]([OH:23])=O)[N:9]=2)=[CH:4][CH:3]=1.[CH2:24]([Cl:27])[CH2:25][Cl:26].[CH:28]1[CH:29]=[CH:30][C:31]2[N:36](O)N=[N:34][C:32]=2[CH:33]=1.[CH:38]([N:41]([CH2:45]C)C(C)C)(C)[CH3:39].CN(C=[O:51])C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:11](=[O:19])[N:10]([CH2:20][C:21]([NH:34][CH:32]([C:33]3[CH:28]=[CH:29][CH:30]=[C:25]([Cl:26])[C:24]=3[Cl:27])[CH2:31][NH:36][C:45](=[O:51])[NH:41][CH2:38][CH3:39])=[O:23])[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59536724[3-(4-Chlorophenyl)-5-oxo-4-(3,3,3-trifluoropropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acid

Product 1

HCID 595368312-[3-(4-Chlorophenyl)-5-oxo-4-(3,3,3-trifluoropropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-{1-(2,3-dichlorophenyl)-2-[(ethylcarbamoyl)amino]ethyl}acetamide

Procedure

Of the compound from Example 177A, 145 mg (0.42 mmol), 143 mg (0.46 mmol) of the compound from Example 154A, 96 mg (0.50 mmol) of EDC, 67 mg (0.50 mmol) of HOBt and 87 μl (0.50 mmol) of N,N-diisopropylethylamine were stirred in 4.9 ml of DMF at RT for 1 h. The entire solution was purified by preparative HPLC [Method 20]. The product fraction was freed from the solvents on a rotary evaporator and the residue was dried in an HV. This gave 150 mg (58% of theory) of the title compound.

Workup

  1. customThe entire solution was purified by preparative HPLC [Method 20]
  2. customThe product fraction was freed from the solvents on a rotary evaporator
  3. customthe residue was dried in an HV

Sources & evidence

ORD record
ord-df7a0da080e143d5b8e2b2ee63251caf
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

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