1,2-Dichloroethane → HCID 15870251, compound

HRID 1740601Notes

Reaction equation

HRID 1740601 reaction equation
[F:1][C:2]([F:23])([F:22])[CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:8]=[CH:7][C:6]=1[CH2:18][C:19]([OH:21])=O.[C:24]([CH:27]1[CH2:32][N:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:39])[CH2:30][CH2:29][NH:28]1)(=[O:26])[NH2:25].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>CN(C=O)C>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:11][C:9]1[CH:8]=[CH:7][C:6]([CH2:18][C:19]([N:28]2[CH2:29][CH2:30][N:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH3:39])[CH2:32][CH:27]2[C:24](=[O:26])[NH2:25])=[O:21])=[C:5]([O:4][CH2:3][C:2]([F:1])([F:23])[F:22])[CH:10]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 154305682-Carbamoyl-4-(2-methylphenyl)piperazineHCID 54364423HCID 54364423, compound

Product 1

HCID 15870251HCID 15870251, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(2,2,2-trifluoroethoxy)-4-(2-pyridyloxy)phenylacetic acid (0.10 g, 0.31 mmol) from Step 4 above and 2-carbamoyl-4-(2-methylphenyl)piperazine (0.08 g, 0.35 mmol) from Step 4 of Example 1 in DMF (2 mL) was added HOBT (0.06 g, 0.35 mmol), EDC (0.10 g, 0.5 mmol), and DIEA (0.09 mL, 0.5 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 (50 mL) and saturated aqueous NaHCO3 (2×25 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 95:5 CH2Cl2 :MeOH as eluant. The product-containing fractions were evaporated under reduced pressure to give the title compound as an amorphous solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between EtOAc (50 mL) and saturated aqueous NaHCO3 (2×25 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by pressurized silica gel column chromatography
  7. customThe product-containing fractions were evaporated under reduced pressure

Sources & evidence

ORD record
ord-b6ebb032a08345f3b0fd30561bf39a54
Source dataset
uspto-grants-1999_10
Patent number
US05968938

Reaction notes

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