1,2-Dichloroethane → HCID 21837259, compound

HRID 1740621Notes

Reaction equation

HRID 1740621 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1)[CH3:2].[F:15][C:16]([F:30])([F:29])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26](O)=[O:27].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[F:15][C:16]([F:29])([F:30])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26]([N:12]1[CH2:11][CH2:10][N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[CH:4]=2)[CH2:14][CH2:13]1)=[O:27]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 18700172HCID 18700172, compoundHCID 199114731-(3-Ethylphenyl)piperazine

Product 1

HCID 21837259HCID 21837259, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3-ethylphenyl)piperazine from the previous step was dissolved in 1 mL dry DMF, and to the solution was added 0.03 g (0.128 mmol) 2-(2,2,2-trifluoroethoxy)phenylacetic acid, 0.017 g (0.128 mmol) HOBT, and 0.024 g (0.128 mmol) EDC. The reaction was stirred for 2 days, after which time the solvent was removed in vacuo and the resulting residue partitioned between EtOAc/H2O. The aqueous phase was extracted with EtOAc and the combined organic phases were washed with H2O, brine, dried over Na2SO4 and filtered. Removal of the solvent and subsequent purification via preparative TLC (2:1 Hexane/EtOAc) yielded the title compound as the free base. This was dissolved in 20 mL EtOAc and an excess of ethanolic HCl was added. The solvent was removed to give the Hcl salt of the title compound.

Workup

  1. customafter which time the solvent was removed in vacuo
  2. customthe resulting residue partitioned between EtOAc/H2O
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washthe combined organic phases were washed with H2O, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customRemoval of the solvent and subsequent purification via preparative TLC (2:1 Hexane/EtOAc)

Sources & evidence

ORD record
ord-66f289cd132b4e0f96507ae2354e72f1
Source dataset
uspto-grants-1999_10
Patent number
US05968938

Reaction notes

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