Triethylamine → HCID 11949616, compound

HRID 2421932Notes

Reaction equation

HRID 2421932 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([CH2:8][CH2:9][NH2:10])=[N:6][CH:7]=1.C(N(CC)CC)C.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23]>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][C:5]([CH2:8][CH2:9][NH:10][C:22](=[O:23])[C:21]2[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=2[C:19]([F:18])([F:29])[F:30])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 63317696HCID 63317696, compound

Product 1

HCID 11949616HCID 11949616, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 0.06 g of 2-(5-bromopyrimidin-2-yl)ethanamine (3.0 mmol) and triethylamine (0.03 g, 1.0 equivalent) in THF (5 ml), at room temperature whilst stirring, was added the 2-trifluoromethyl benzoyl chloride (0.062 g, 1.0 equivalent) and the mixture was left to stir at room temperature overnight. The solvent was removed by evaporation in vacuo and saturated sodium bicarbonate (10 mls) was added. The mixture was extracted with dichloromethane and the organic phase was collected, dried over MgSO4, and evaporated in vacuo to give the crude product which was purified by chromatography on silica using 1:1 heptane/ethyl acetate to yield to 0.036 g of N-[2-(5-bromopyrimidin-2-yl)ethyl]-2-(trifluoromethyl)benzamide (Compound A-1) (32%).

Workup

  1. waitthe mixture was left
  2. customThe solvent was removed by evaporation in vacuo and saturated sodium bicarbonate (10 mls)
  3. additionwas added
  4. extractionThe mixture was extracted with dichloromethane
  5. customthe organic phase was collected
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo
  8. customto give the crude product which
  9. customwas purified by chromatography on silica using 1:1 heptane/ethyl acetate

Sources & evidence

ORD record
ord-e3a87bdb6ccb47abae1c73fd50e3d20b
Source dataset
uspto-grants-2011_06
Patent number
US07960391B2

Reaction notes

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