1,2-Dichloroethane → HCID 21837255, compound

HRID 1740591Notes

Reaction equation

HRID 1740591 reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][O:4][CH:5]([C:9]1C=C[CH:12]=[CH:11][CH:10]=1)C(O)=O.[C:17]([CH:20]1[CH2:25][N:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])[CH2:23][CH2:22][NH:21]1)(=[O:19])[NH2:18].C1C=CC2N([OH:42])N=NC=2C=1.C(Cl)CCl.CCN([CH:53]([CH3:55])[CH3:54])C(C)C>CN(C=O)C>[F:1][C:2]([F:15])([F:16])[CH2:3][O:4][C:5]1[CH:9]=[CH:10][CH:11]=[CH:12][C:55]=1[CH2:53][C:54]([N:21]1[CH2:22][CH2:23][N:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])[CH2:25][CH:20]1[C:17](=[O:19])[NH2:18])=[O:42]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 154305682-Carbamoyl-4-(2-methylphenyl)piperazineHCID 2183723282027-57-4

Product 1

HCID 21837255HCID 21837255, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(2,2,2-trifluoroethoxyphenylacetic acid (0.10 g, 0.45 mmol) from Step 2 above and 2-carbamoyl-4-(2-methylphenyl)piperazine (0.10 g, 0.46 mmol) from Step 4 of Example 1 in DMF (15 mL) was added HOBT (0.075 g, 0.5 mmol), EDC (0.22 g, 0.75 mmol), and DIEA (0.13 mL, 0.75 mmol). The solution was stirred at ambient temperature for 14 h and the solvent was removed under reduced pressure. The residue was partitioned between EtOAc (100 mL) and 0.25 M aqueous citric acid (25 mL). The organic phase was separated and washed with H2O (25 mL), saturated aqueous NaHCO3 (25 mL), and brine (25 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel coulmn chromatography using 5:95 MeOH:CH2Cl2 as eluant. The title compound was obtained as an amorphous solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between EtOAc (100 mL) and 0.25 M aqueous citric acid (25 mL)
  3. customThe organic phase was separated
  4. washwashed with H2O (25 mL), saturated aqueous NaHCO3 (25 mL), and brine (25 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by pressurized silica gel coulmn chromatography

Sources & evidence

ORD record
ord-82ece4062a4946c8b4f2d5546d604110
Source dataset
uspto-grants-1999_10
Patent number
US05968938

Reaction notes

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