1,2-Dichloroethane → HCID 86597097, compound

HRID 1455551Notes

Reaction equation

HRID 1455551 reaction equation
C(Cl)CCl.[C:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=1[N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][C:25](O)=[O:26])[CH2:20][CH2:19]1)(=[O:7])[NH2:6].[F:28][C:29]([F:45])([F:44])[C:30]1[CH:31]=[C:32]([S:40]([NH2:43])(=[O:42])=[O:41])[CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1.CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.CN(C=O)C>[F:39][C:36]([F:37])([F:38])[C:34]1[CH:33]=[C:32]([S:40]([NH:43][C:25](=[O:26])[CH2:24][CH:21]2[CH2:20][CH2:19][N:18]([C:9]3[CH:10]=[C:11]([C:14]([F:15])([F:17])[F:16])[CH:12]=[CH:13][C:8]=3[C:5]([NH2:6])=[O:7])[CH2:23][CH2:22]2)(=[O:42])=[O:41])[CH:31]=[C:30]([C:29]([F:45])([F:28])[F:44])[CH:35]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 27831653,5-bis(trifluoromethyl)benzenesulfonamideHCID 68442763[1-(2-Carbamoyl-5-trifluoromethyl-phenyl)-piperidin-4-yl]-acetic acid

Product 1

HCID 86597097HCID 86597097, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

0.46 g of 2-fluoro-4-(trifluoromethyl)benzamide are added to a suspension of 1.8 g K2CO3 and 0.8 g of piperidin-4-yl acetic acid hydrochloride In 12 ml of DMSO, the mixture obtained is stirred for 4 h at 150°, solvent is evaporated, the evaporation residue obtained is suspended in MeOH and filtrated. The filtrate obtained is concentrated and subjected to chromatography on silica gel. [1-(2-Carbamoyl-5-trifluoromethyl-phenyl)-piperidin-4-yl]-acetic acid is obtained. 300 mg of EDC are added to a solution of 260 mg of [1-(2-carbamoyl-5-trifluoromethyl-phenyl)-piperidin-4-yl]-acetic acid, 230 mg of 3,5-bis-trifluoromethyl-benzenesulfonamide, 200 mg of DIEA and 90 mg of DMAP in 4 ml of DMF. The mixture obtained is stirred for 3 days at RT, solvent is evaporated in vacuo and the evaporation residue obtained is treated with EtAc. The mixture obtained is washed with 1 N HCl, saturated aqueous NaHCO3 solution and brine, dried, concentrated in vacuo and subjected to chromatography on silica gel. 2-{4-[2-(3,5-Bis-trifluoromethyl-benzenesulfonylamino)-2-oxo-ethyl]-piperidin-1-yl}-4-trifluoromethyl-benzamide is obtained.

Workup

  1. customThe mixture obtained
  2. customsolvent is evaporated in vacuo
  3. customthe evaporation residue obtained
  4. additionis treated with EtAc
  5. customThe mixture obtained
  6. washis washed with 1 N HCl, saturated aqueous NaHCO3 solution and brine
  7. customdried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-332ce80768094c38aa3d78fae640c5f7
Source dataset
uspto-grants-2009_01
Patent number
US07482462B2

Reaction notes

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