Acetic Anhydride → HCID 53920834, compound

HRID 1646251Notes

Reaction equation

HRID 1646251 reaction equation
[C:1]1([C:7]2[C:15]([CH:16]=[CH:17][C:18]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]3[CH2:26][OH:27])=[O:19])=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29].C(OCC)(=O)C>N1C=CC=CC=1>[C:1]1([C:7]2[C:15]([CH:16]=[CH:17][C:18]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]3[CH2:26][O:27][C:28](=[O:30])[CH3:29])=[O:19])=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 53875970HCID 53875970, compound

Product 1

HCID 53920834HCID 53920834, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-[3-(2-Phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-hydroxymethylpiperidine (trans isomer) (0.50 g) was added to a stirred solution of acetic anhydride (0.16 g) in pyridine (5 ml) at room temperature, and stirred at room temperature for 3 hours. Ethyl acetate was added to the reaction mixture and washed with 1N aqueous sodium hydroxide solution, water and saturated sodium chloride aqueous solution, then dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (50 g) with a mixture of chloroform and acetone (20:1) as an eluent. The fractions containing the objective compound were combined and evaporated in vacuo to give 1-[3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-acetoxymethylpiperidine (trans isomer) (0.35 g) as an oil.

Workup

  1. washwashed with 1N aqueous sodium hydroxide solution, water and saturated sodium chloride aqueous solution
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel (50 g) with a mixture of chloroform and acetone (20:1) as an eluent
  5. additionThe fractions containing the objective compound
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-e9ed1936d1aa45c6bba1ea7b18737298
Source dataset
uspto-grants-1993_01
Patent number
US05179103

Reaction notes

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