1,2-Dichloroethane → HCID 18700097, compound

HRID 2289338Notes

Reaction equation

HRID 2289338 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.[NH:17]1[CH2:22][CH2:21][CH:20]([N:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26][CH2:25][C:24]2=[O:33])[CH2:19][CH2:18]1.C1C=CC2N([OH:43])N=NC=2C=1.C(Cl)CCl.CCN([CH:54]([CH3:56])[CH3:55])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:56]=1[CH2:54][C:55]([N:17]1[CH2:22][CH2:21][CH:20]([N:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26][CH2:25][C:24]2=[O:33])[CH2:19][CH2:18]1)=[O:43]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 107281851-(piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-oneHCID 2183723282027-57-4

Product 1

HCID 18700097HCID 18700097, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(2,2,2-trifluoroethoxyphenyl-acetic acid (0.20 g, 0.90 mmol) from Step 2 of Example 16 and 1-(piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one prepared by the method of Ogawa, et al., J. Med. Chem. (1993), vol. 36, pp. 2011-2017) (0.24 g, 0.90 mmol) in DMF (15 mL) was added HOBT (0.15 g, 1.0 mmol), EDC (0.44 g, 1.5 mmol), and DIEA (0.3 mL, 1.7 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 column chromatography using 97:2 CH2Cl2 :MeOH as eluant 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 (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 column chromatography

Sources & evidence

ORD record
ord-2fd2cce8bbc4435c8bc8a0db029dd019
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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