Triethylamine → HCID 66811752, compound

HRID 1097417Notes

Reaction equation

HRID 1097417 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([C:16]3[N:21]4[N:22]=[C:23]([C:25]5[CH:26]=[N+:27]([O-])[CH:28]=[CH:29][CH:30]=5)[N:24]=[C:20]4[N:19]=[CH:18][CH:17]=3)[CH:9]=[CH:10][C:11]=2[O:12][CH:13]([F:15])[F:14])[CH2:3][CH2:2]1.C[CH2:33][N:34](CC)CC.[Si]([C:43]#[N:44])(C)(C)C>CC#N>[C:33]([C:28]1[CH:29]=[CH:30][C:25]([C:23]2[N:24]=[C:20]3[N:19]=[CH:18][CH:17]=[C:16]([C:8]4[CH:9]=[CH:10][C:11]([O:12][CH:13]([F:15])[F:14])=[C:6]([O:5][CH2:4][CH:1]5[CH2:3][CH2:2]5)[CH:7]=4)[N:21]3[N:22]=2)=[CH:26][N:27]=1)#[N:34].[C:43]([C:26]1[N:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:23]1[N:24]=[C:20]2[N:19]=[CH:18][CH:17]=[C:16]([C:8]3[CH:9]=[CH:10][C:11]([O:12][CH:13]([F:15])[F:14])=[C:6]([O:5][CH2:4][CH:1]4[CH2:3][CH2:2]4)[CH:7]=3)[N:21]2[N:22]=1)#[N:44]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 24944540HCID 24944540, compound2×

Product 2

HCID 66811752HCID 66811752, compoundYield 72%HCID 66811861HCID 66811861, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In CH3CN, dissolved was 3-[7-{3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl}-[1,2,4]triazolo[1,5-a]pyri midine-2-yl]-pyridine-N-oxide (Compound 102) (0.5 g, 1.17 mmol). While stirring the solution, Et3N (0.2 g, 2.0 mmol) and TMSCN (0.47 g, 4.70 mmol) were slowly added dropwise thereto, and the resultant mixture was heated under reflux. The solvent was distilled under reduced pressure, and NaHCO3(aq) was added to the residue. The mixture was extracted three times with CH2Cl2, and the extract was washed twice with brine, dried over MgSO4, filtered, and evaporated under reduced pressure to remove solvent. The mixture was purified via silica gel column chromatography (MC/EA, 2/1) to obtain the desired compound, 2-(2-cyano-pyridin-5-yl)-7-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 123) (0.37 g, 72%) and 2-(6-cyano-pyridin-5-yl)-7-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 124) (0.12 g, 24%).

Workup

  1. additionwere slowly added dropwise
  2. temperatureunder reflux
  3. distillationThe solvent was distilled under reduced pressure, and NaHCO3(aq)
  4. additionwas added to the residue
  5. extractionThe mixture was extracted three times with CH2Cl2
  6. washthe extract was washed twice with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customto remove solvent
  11. customThe mixture was purified via silica gel column chromatography (MC/EA, 2/1)

Sources & evidence

ORD record
ord-99647e56c7054a1b89781bd7b0e32c56
Source dataset
uspto-grants-2012_03
Patent number
US08143262B2

Reaction notes

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