Water → HCID 86601246, compound

HRID 2251977Notes

Reaction equation

HRID 2251977 reaction equation
C[Al](C)C.[CH2:5]([NH2:8])[CH2:6][NH2:7].CO[C:11]([C:13]1[N:14]=[N:15][N:16]([CH2:24][C:25]2[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=2)[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O.O>C1(C)C=CC=CC=1>[F:36][C:35]([F:37])([F:38])[C:27]1[CH:26]=[C:25]([CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=1)[CH2:24][N:16]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:13]([C:11]2[NH:7][CH2:6][CH2:5][N:8]=2)[N:14]=[N:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 3301EthylenediamineHCID 16682925TrimethylaluminumHCID 86601247HCID 86601247, compound

Product 1

HCID 86601246HCID 86601246, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of Me3Al (1.36 mL, 2M soln in toluene) at 0° C. under N2, add ethylenediamine (185 μL, 0.36 mmol) and stir for several minutes warming to RT. Add 1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazole-4-carboxylic acid methyl ester (750 mg, 1.69 mmol) dissolved in toluene to this solution. Reflux reaction for 3.5 hours at 110° C. Cool to RT and stir for 12 hours. Quench reaction with MeOH (2 mL), add H2O (2 mL) and extract with CH2Cl2 (4 mL×2). Dry over Na2SO4 and concentrate to afford title compound (30 mg, 4%). MS (IS) 440.1 (M+1).

Workup

  1. temperatureReflux
  2. customreaction for 3.5 hours at 110° C
  3. temperatureCool to RT
  4. stirringstir for 12 hours
  5. customQuench
  6. customreaction with MeOH (2 mL)
  7. extractionextract with CH2Cl2 (4 mL×2)
  8. dry with materialDry over Na2SO4
  9. concentrationconcentrate

Sources & evidence

ORD record
ord-7486854bc5b543db95f639e001bcac80
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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