Acetoxyacetyl chloride → HCID 67364100, compound

HRID 245726Notes

Reaction equation

HRID 245726 reaction equation
Cl.[Br:2][C:3]1[N:4]=[C:5]([C@@H:13]2[CH2:17][CH2:16][NH:15][CH2:14]2)[N:6]2[CH:11]=[CH:10][N:9]=[C:8]([CH3:12])[C:7]=12.C(N(CC)C(C)C)(C)C.[C:27]([O:30][CH2:31][C:32](Cl)=[O:33])(=[O:29])[CH3:28]>ClCCl>[C:27]([O:30][CH2:31][C:32]([N:15]1[CH2:16][CH2:17][C@@H:13]([C:5]2[N:6]3[CH:11]=[CH:10][N:9]=[C:8]([CH3:12])[C:7]3=[C:3]([Br:2])[N:4]=2)[CH2:14]1)=[O:33])(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 26297Acetoxyacetyl chlorideHCID 81531DiisopropylethylamineHCID 67365099HCID 67365099, compound

Product 1

HCID 67364100HCID 67364100, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To (R)-1-bromo-8-methyl-3-(pyrrolidin-3-yl)imidazo[1,5-a]pyrazine hydrochloride (0.15 mmol, 50 mg) in dichloromethane (4 ml) and N,N-diisopropylethylamine (0.889 mmol, 0.155 ml) at 0° C. was added dropwise a solution of acetoxyacetyl chloride (0.187 mmol, 0.020 ml) in dichloromethane (0.5 ml). After stirring at room temperature for one hour the reaction mixture was diluted with dichloromethane, washed with saturated aqueous sodium hydrogencarbonate solution, water, brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel; dichloromethane with gradient 0 to 10% methanol) to give (R)-2-(3-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)pyrrolidin-1-yl)-2-oxoethyl acetate (45 mg).

Workup

  1. washwashed with saturated aqueous sodium hydrogencarbonate solution, water, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography (silica gel; dichloromethane with gradient 0 to 10% methanol)

Sources & evidence

ORD record
ord-f7a7729bb1a747b0bb7960b08a82b8d1
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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