Potassium Carbonate → HCID 67606429, compound

HRID 1626972Notes

Reaction equation

HRID 1626972 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:15].Br[CH2:17][C:18]#[N:19].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[O:15][CH2:17][C:18]#[N:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 67606759HCID 67606759, compound

Product 1

HCID 67606429HCID 67606429, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-ol (25 mg, 0.093 mmol), bromoacetonitrile (34 mg, 0.28 mmol, 3 equiv) and potassium carbonate (64 mg, 0.47 mmol, 5 equiv) were combined in dimethylsulfoxide (1 mL) and placed into a preheated oil bath at 80° C. for 30 minutes. The mixture was cooled to ambient temperature, filtered and purified by preparative HPLC (20 to 95% water containing 0.5% trifluoroacetic acid: acetonitrile containing 0.5% trifluoroacetic acid). The appropriate fractions were poured into sodium bicarbonate (50 mL, aqueous saturated) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound as a light brown solid: 1H-NMR (400 MHz, CDCl3) δ 7.55 (1H, d, J=9.2 Hz), 7.41 (1H, d, J=9.0 Hz), 4.91 (2H, s), 4.53 (2H, d, J=7.1 Hz), 1.45-1.35 (1H, m), 0.71-0.66 (2H, m), 0.52-0.48 (2H, m) ppm; high resolution mass spectrometry (ES+) m/z 307.0187 [(M+H)+; calculated for C12H12BrN4O: 307.0189].

Workup

  1. filtrationfiltered
  2. custompurified by preparative HPLC (20 to 95% water containing 0.5% trifluoroacetic acid: acetonitrile containing 0.5% trifluoroacetic acid)
  3. additionThe appropriate fractions were poured into sodium bicarbonate (50 mL, aqueous saturated)
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. dry with materialThe combined organic extracts were dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8608dea1962c4e57a97d5bdb4c742b38
Source dataset
uspto-grants-2014_07
Patent number
US08785481B2

Reaction notes

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