Triethylamine → HCID 178461109, compound

HRID 1182895Notes

Reaction equation

HRID 1182895 reaction equation
C(N(CC)CC)C.[C:8]([C@@H:12]1[CH2:17][CH2:16][C@H:15]([NH2:18])[CH2:14][CH2:13]1)([CH3:11])([CH3:10])[CH3:9].[F:19][CH:20]([C:22]1[C:27]([Cl:28])=[C:26](Cl)[N:25]2[N:30]=[CH:31][N:32]=[C:24]2[N:23]=1)[CH3:21]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:8]([C@@H:12]1[CH2:13][CH2:14][C@H:15]([NH:18][C:26]2[N:25]3[N:30]=[CH:31][N:32]=[C:24]3[N:23]=[C:22]([CH:20]([F:19])[CH3:21])[C:27]=2[Cl:28])[CH2:16][CH2:17]1)([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 860365495-(1-Fluoroethyl)-6,7-dichloro-[1,2,4]triazolo[1,5-a]pyrimidineHCID 178445676HCID 178445676, compound

Product 1

HCID 178461109HCID 178461109, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolvent

Procedure

0.220 g (2.2 mmol) Triethylamine, a spatula tip of tetrabutylammonium iodide and 0.340 g (2.2 mmol) of cis-4-tert-butylcyclohexylamine were added successively to a solution of 0.470 g (2.0 mmol) of 5-(1-fluoroethyl)-6,7-dichloro-[1,2,4]triazolo[1,5-a]pyrimidine in 15 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 water. The organic phase was separated, dried and the solvent was evaporated under reduced pressure. Treatment of the resulting residue with hexane yielded 0.540 g (1.5 mmol, 76% of theory) of the title compound having a melting point of 138-139° 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 water
  8. customThe organic phase was separated
  9. customdried
  10. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b3856b4e115446bdb110b713d9e0fb18
Source dataset
uspto-grants-2014_03
Patent number
US08664235B2

Reaction notes

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