Dimethylformamide → HCID 68782578, compound

HRID 2266004Notes

Reaction equation

HRID 2266004 reaction equation
Cl[C:2]1[C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[N:3]=1.[CH3:17][O:18][CH:19]1[CH2:23][CH2:22][NH:21][CH2:20]1.CN(C=O)C>CCOC(C)=O>[CH3:17][O:18][CH:19]1[CH2:23][CH2:22][N:21]([C:2]2[C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[N:3]=2)[CH2:20]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 113554473-MethoxypyrrolidineHCID 723356323-(2-Chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid

Product 1

HCID 68782578HCID 68782578, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-(2-chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid (50 mg, 0.198 mmol) in 3-methoxy-pyrrolidine (40 mg, 0.396 mmol) was added DMF (1.0 ml). The mixture was stirred for 12 hours at room temperature. The reaction mixture was diluted with EtOAc and then washed two times with 1N-HCl and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was chromatographed to yield the 3-[2-(3-methoxy-pyrrolidin-1-yl)-6-trifluoromethyl-pyridin-3-yl]-acrylic acid (59 mg, 98%).

Workup

  1. washwashed two times with 1N-HCl and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was chromatographed

Sources & evidence

ORD record
ord-7cdb31048bb84fca974a037774f49f65
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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