Acetyl chloride → HCID 24955342, compound

HRID 2389943Notes

Reaction equation

HRID 2389943 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[CH:14]=[CH:13][C:12]4[O:15][CH2:16][CH2:17][C:11]=4[N:10]3[C:18]=2[CH2:19][C:20]#[N:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:29](Cl)(=[O:31])[CH3:30]>N.C(O)C.C(=O)([O-])O.[Na+].[Co]>[C:1]1([C:7]2[N:8]=[C:9]3[CH:14]=[CH:13][C:12]4[O:15][CH2:16][CH2:17][C:11]=4[N:10]3[C:18]=2[CH2:19][CH2:20][NH:21][C:29](=[O:31])[CH3:30])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 53310700HCID 53310700, compound

Product 1

HCID 24955342HCID 24955342, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 104730CobaltCatalystHCID 516892Sodium BicarbonateSolventHCID 22020343Ethanol, reaction products with ammonia, distn. residuesSolvent

Procedure

To a solution (5 mL) of (7-phenyl-1,2-dihydrofuro[2,3-e]imidazo[1,2-a]pyridin-8-yl)acetonitrile (17.0 mg, 0.062 mmol) in 2M ammonia/ethanol was added Raney cobalt (500 mg), and the mixture was stirred at room temperature for 2.5 hr under a hydrogen atmosphere. The catalyst was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (2 mL), triethylamine (17.3 μL, 0.124 mmol) and acetyl chloride (5.3 μL, 0.074 mmol) were added, and the mixture was stirred at room temperature for 20 min. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90) and recrystallization (ethyl acetate/hexane) to give the title compound (12.9 mg, yield 65%).

Workup

  1. filtrationThe catalyst was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in tetrahydrofuran (2 mL)
  4. stirringthe mixture was stirred at room temperature for 20 min
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90) and recrystallization (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4cca526784504e1e9e61886a16ff1b78
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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