Bromoacetonitrile → HCID 17895494, compound

HRID 1383837Notes

Reaction equation

HRID 1383837 reaction equation
[C:1]1([C:7]2[N:11]3[NH:12][C:13](=[O:22])[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:15][C:10]3=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:26][C:27]#[N:28]>CN(C=O)C>[C:1]1([C:7]2[N:11]3[N:12]=[C:13]([O:22][CH2:26][C:27]#[N:28])[C:14]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:15][C:10]3=[N:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 21187496HCID 21187496, compound

Product 1

HCID 17895494HCID 17895494, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3,7-diphenyl-1,2,4-triazolo[4,3-b]pyridazin-6-one (from Example 73, Step a) (0.4021 g, 1.39 mmol) in anhydrous DMF (20 ml) under nitrogen was added sodium hydride (60% dispersion in oil, 84.0 mg, 2.10 mmol) and the mixture was stirred at room temperature for 30 min,. then at 80° C. for 20 min. After allowing to cool, bromoacetonitrile (0.146 ml, 2.10 mmol) was added dropwise and the mixture was stirred at room temperature for 14 h. The mixture was then partitioned between ethyl acetate (100 ml) and water (100 ml), adding saturated aqueous NaCl to aid in the separation of the layers. The aqueous layer was extracted further with ethyl acetate (2×100 ml) and the combined organic extracts were dried (Na2SO4), and evaporated in vacua. The residue was purified by flash chromatography (silica gel 2% MeOH/CH2Cl2) to afford 0.4566 g (100%) of the title compound as a buff solid: 1H NMR (360 MHz, CDCl3) δ5.11 (2 H, s), 7.52-7.63 (8 H, m), 8.12 (1 H, s), 8.45 (2 H, m); MS (ES+) m/e 328 [MH]+.

Workup

  1. waitthen at 80° C. for 20 min
  2. temperatureto cool
  3. stirringthe mixture was stirred at room temperature for 14 h
  4. customThe mixture was then partitioned between ethyl acetate (100 ml) and water (100 ml)
  5. additionadding saturated aqueous NaCl
  6. customto aid in the separation of the layers
  7. extractionThe aqueous layer was extracted further with ethyl acetate (2×100 ml)
  8. dry with materialthe combined organic extracts were dried (Na2SO4)
  9. customevaporated in vacua
  10. customThe residue was purified by flash chromatography (silica gel 2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-aae81edb8c3546cebadc376df3b8fb79
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

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