1,2-Dichloroethane → 1-(3-Chloro-2-(2,2,2-trifluoroethoxy)phenylacetyl)-2-carbamoyl-4-(2-methylphenyl)piperazine

HRID 1740606Notes

Reaction equation

HRID 1740606 reaction equation
[F:1][C:2]([F:17])([F:16])[CH2:3][O:4][C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:12][C:13]([OH:15])=O.[C:18]([CH:21]1[CH2:26][N:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])[CH2:24][CH2:23][NH:22]1)(=[O:20])[NH2:19].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:11][C:10]1[C:5]([O:4][CH2:3][C:2]([F:1])([F:17])[F:16])=[C:6]([CH2:12][C:13]([N:22]2[CH2:23][CH2:24][N:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[CH3:33])[CH2:26][CH:21]2[C:18](=[O:20])[NH2:19])=[O:15])[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 154305682-Carbamoyl-4-(2-methylphenyl)piperazineHCID 539993942-(2,2,2-Trifluoroethoxy)-3-chlorophenylacetic acid

Product 1

HCID 218372181-(3-Chloro-2-(2,2,2-trifluoroethoxy)phenylacetyl)-2-carbamoyl-4-(2-methylphenyl)piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(2,2,2-trifluoroethoxy)-3-chlorophenylacetic acid (0.14 g, 0.53 mmol) from Step 4 above, 2-carbamoyl-4-(2-methylphenyl)piperazine (0.12 g, 0.53 mmol) from Step 4 of Example 1, and HOBT (0.08 g, 0.53 mmol) in DMF (5 mL) was added EDC (0.15 g, 0.8 mmol) and DIEA (0.14 mL, 0.8 mmol). The mixture was stirred at ambient temperature for 14 h. The solvent was removed under reduced pressure and the residue was purified by preparative reverse phase HPLC using a H2O:CH3CN gradient containing 0.1% TFA. The product-containing fractions were lyophilized to give the title compound as an amorphous powder.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by preparative reverse phase HPLC
  3. additionCH3CN gradient containing 0.1% TFA

Sources & evidence

ORD record
ord-59047cab10664b81b97b07b9302d2f8f
Source dataset
uspto-grants-1999_10
Patent number
US05968938

Reaction notes

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