Dimethylformamide → HCID 11711808, compound

HRID 1994138Notes

Reaction equation

HRID 1994138 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].Cl[C:25]1[N:30]=[C:29](Cl)[CH:28]=[CH:27][N:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C[N:39](C=O)C>C1COCC1.O>[NH2:39][C:25]1[N:30]=[C:29]([O:18][C:14]2[CH:13]=[C:12]([CH2:11][CH2:10][C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:20]([F:21])([F:22])[F:23])[CH:4]=3)=[O:19])[CH:17]=[CH:16][CH:15]=2)[CH:28]=[CH:27][N:26]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 775312,4-DichloropyrimidineHCID 58674349N-[4-Chloro-3-(trifluoromethyl)phenyl]-3-hydroxybenzenepropanamide

Product 1

HCID 11711808HCID 11711808, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-[4-chloro-3-(trifluoromethyl)phenyl]-3-(3-hydroxyphenyl)propanamide (1.63 g, 4.70 mmol), 2,4-dichloropyrimidine (0.883 g, 5.90 mmol) and cesium carbonate (2.32 g, 7.10 mmol) in THF (60 mL) containing a drop of DMF was heated at reflux overnight. After cooling to rt, the reaction mixture was diluted with water and extracted with EtOAc. The combined organic solutions were washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography to give the title compound (1.60 g, 77%). LCMS, FA: Rt=1.28 min, [MH+ 520.2].

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionextracted with EtOAc
  4. washThe combined organic solutions were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e529e2b52e3c4b3fba30363a8fb9645d
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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