1,2-Dichloroethane → N-[(5-chloropyridin-2-yl)methyl]-4,4,5,5,5-pentafluoropentanamide

HRID 2203340Notes

Reaction equation

HRID 2203340 reaction equation
[F:1][C:2]([F:12])([C:8]([F:11])([F:10])[F:9])[CH2:3][CH2:4][C:5]([OH:7])=O.Cl.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][NH2:22])=[N:19][CH:20]=1.C(Cl)CCl.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][NH:22][C:5](=[O:7])[CH2:4][CH2:3][C:2]([F:1])([F:12])[C:8]([F:11])([F:10])[F:9])=[N:19][CH:20]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 234231634,4,5,5,5-Pentafluoropentanoic acidHCID 56973027(5-Chloropyridin-2-yl)methanamine hydrochloride

Product 1

HCID 86678976N-[(5-chloropyridin-2-yl)methyl]-4,4,5,5,5-pentafluoropentanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4,4,5,5,5-pentafluoropentanoic acid (6.44 g, 33.5 mmol) and the intermediate from Step E (5.0 g, 27.9 mmol) in DCM (100 mL) was added EDC (7.49 g, 39.1 mmol) followed by DIEA (24.4 mL, 140 mmol). After stirring the reaction at room temperature for 2 hours, it was diluted with DCM (100 mL), and washed with water (2×). The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give a colorless oil. m/z=316.8 (M+H).

Workup

  1. customthe reaction at room temperature for 2 hours
  2. washwashed with water (2×)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a colorless oil

Sources & evidence

ORD record
ord-88a381e1254f4812899ce0cc240ddd39
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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