Triethylamine → HCID 44128882, compound

HRID 1182896Notes

Reaction equation

HRID 1182896 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([NH2:17])[CH3:16])=[CH:11][CH:10]=1.[CH3:18][C:19]1[C:24]([Cl:25])=[C:23](Cl)[N:22]2[N:27]=[CH:28][N:29]=[C:21]2[N:20]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Cl:25][C:24]1[C:19]([CH3:18])=[N:20][C:21]2[N:22]([N:27]=[CH:28][N:29]=2)[C:23]=1[NH:17][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([F:8])=[CH:10][CH:11]=1)[CH3:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineHCID 866092416,7-Dichloro-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 44128882HCID 44128882, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolvent

Procedure

0.300 g (3.0 mmol) Triethylamine, a spatula tip of tetrabutylammonium iodide and 0.514 g (3.7 mmol) of (S)-1-(4-fluorophenyl)-ethylamine were added successively to a solution of 0.500 g (2.5 mmol) of 5-methyl-6,7-dichloro-[1,2,4]triazolo[1,5-a]pyrimidine in 10 ml of toluene under stirring. The reaction mixture was heated at reflux for 5 hours and then stirred for another 12 hours at room temperature. The solvent was evaporated under reduced pressure and dichloromethane was added to the resulting residue. The resulting reaction mixture was washed with 2N hydrochloric acid and with water. The organic phase was separated, dried and the solvent was evaporated under reduced pressure. Treatment of the resulting residue with hexane yielded 0.520 g (1.7 mmol, 68% of theory) of the title compound having a melting point of 103-104° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5 hours
  3. stirringstirred for another 12 hours at room temperature
  4. customThe solvent was evaporated under reduced pressure and dichloromethane
  5. additionwas added to the resulting residue
  6. customThe resulting reaction mixture
  7. washwas washed with 2N hydrochloric acid and with water
  8. customThe organic phase was separated
  9. customdried
  10. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b5386b3b4e5045c28f3fcca1a4db6c62
Source dataset
uspto-grants-2014_03
Patent number
US08664235B2

Reaction notes

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