Triethylamine → HCID 86711917, compound

HRID 1475223Notes

Reaction equation

HRID 1475223 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[N:9][C:8]([C:12]([NH2:14])=O)=[N:7]1.CCN(CC)CC.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[N:9][C:8]([C:12]#[N:14])=[N:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 86711916HCID 86711916, compound

Product 1

HCID 86711917HCID 86711917, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 1-(3-bromobenzyl)-5-methyl-1H-1,2,4-triazole-3-carboxamide (50 mg, 0.17 mmol) and Et3N (47 μL, 0.34 mmol) in DCM (2 mL) was slowly added a solution of trifluoroacetic anhydride (29 μL, 0.20 mmol) in DCM (2 mL) at 0° C. The reaction was stirred at 0° C. for 2 h, and was then warmed to RT while stirring overnight. The reaction was then quenched with H2O (3 mL) and washed with NaOH (1N, 5 mL) and brine (2×5 mL) before being concentrated under reduced pressure. The crude product was purified on a Biotage pre-packed silica gel column with a gradient of 12% to 80% EtOAc:Hexanes to afford 1-(3-bromobenzyl)-5-methyl-1H-1,2,4-triazole-3-carbonitrile (39 mg, 83%) as a viscous oil. MS (ES+) C11H9BrN4 requires: 276, 278 found: 277, 279 [M+H]+(1:1).

Workup

  1. temperaturewas then warmed to RT
  2. stirringwhile stirring overnight
  3. customThe reaction was then quenched with H2O (3 mL)
  4. washwashed with NaOH (1N, 5 mL) and brine (2×5 mL)
  5. concentrationbefore being concentrated under reduced pressure
  6. customThe crude product was purified on a Biotage pre-packed silica gel column with a gradient of 12% to 80% EtOAc

Sources & evidence

ORD record
ord-2e75ce55fc8142699108fd615d25c31d
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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