Triethylamine → HCID 22648764, compound

HRID 393144Notes

Reaction equation

HRID 393144 reaction equation
Cl.N1[CH:7]=[CH:6][CH:5]=[N:4][C:3]=1[CH2:8][C:9]([OH:11])=O.[CH2:12](N(CC)CC)C.C(N1C=CN=C1)(N1C=CN=C1)=O.[F:31][C:32]([F:46])([F:45])[C:33]1[C:38]([CH:39]([NH:43][CH3:44])[CH:40]([CH3:42])[CH3:41])=[CH:37][N:36]=[CH:35][N:34]=1>O1CCCC1.O>[CH3:44][N:43]([CH:39]([C:38]1[C:33]([C:32]([F:31])([F:45])[F:46])=[N:34][CH:35]=[N:36][CH:37]=1)[CH:40]([CH3:42])[CH3:41])[C:9](=[O:11])[CH2:8][C:3]1[CH:12]=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 22648743HCID 22648743, compoundHCID 69850562HCID 69850562, compound

Product 1

HCID 22648764HCID 22648764, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.3 g (1.7 mmol) of 2-pyrimidinylacetate hydrochloride and 0.18 g (1.8 mmol) of triethylamine were dissolved in 30 ml of tetrahydrofuran, and 0.28 g (1.7 mmol) of 1,1′-carbonylbis-1H-imidazole was added, followed by stirring at room temperature for 1 hour. Then, 0.4 g (1.7 mmol) of 4-trifluoromethyl-5-[1-(N-methylamino)-2-methylpropyl]pyrimidine was added, followed by heating and refluxing for further 3 hours. To the reaction solution, 100 ml of water was added, followed by extraction with ethyl acetate. The obtained organic layer was washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (developing solvent/n-hexane:ethyl acetate:methanol=4.5:4.5:1) to obtain 0.2 g (yield: 33%) of N-methyl-N-[2-methyl-1-(4-trifluoromethylpyrimidin-5-yl)propyl]-2-pyridylacetamide as colorless transparent crystals (melting point: 99-100° C.).

Workup

  1. temperatureby heating
  2. temperaturerefluxing for further 3 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe obtained organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationEthyl acetate was distilled off under reduced pressure
  7. customthe obtained crude product
  8. customwas purified by silica gel column chromatography (developing solvent/n-hexane:ethyl acetate:methanol=4.5:4.5:1)

Sources & evidence

ORD record
ord-2c4ab87ea38e4c60bbf49d0e4979e24c
Source dataset
uspto-grants-2004_10
Patent number
US06806230B1

Reaction notes

Loading…