Acetic Anhydride → HCID 53920834, compound

HRID 981960Notes

Reaction equation

HRID 981960 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-7e922e40d29d46a3b4532aab1fe76c63
Source dataset
uspto-grants-1991_02
Patent number
US04994453

Reaction notes

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