Acetic Anhydride → 7-Acetoxy-2-pyridin-2-yl-3-quinolin-4-yl-pyrazolo[1,5-a]piperidine

HRID 8272Notes

Reaction equation

HRID 8272 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:16]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)=[C:10]2[CH2:11][CH2:12][CH2:13][CH:14]([OH:15])[N:9]2[N:8]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>N1C=CC=CC=1>[C:27]([O:15][CH:14]1[N:9]2[N:8]=[C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[C:16]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=[CH:19][CH:18]=3)=[C:10]2[CH2:11][CH2:12][CH2:13]1)(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 99241362-Pyridin-2-yl-3-quinolin-4-yl-pyrazolo[1,5-a]piperidin-7-ol

Product 1

HCID 102216207-Acetoxy-2-pyridin-2-yl-3-quinolin-4-yl-pyrazolo[1,5-a]piperidine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-pyridin-2-yl-3-quinolin-4-yl-pyrazolo[1,5-a]piperidin-7-ol (0.04 g, 0.12 mmol) and acetic anhydride (0.2 mL) in pyridine (2 mL) at room temperature is stirred for 24 h. The mixture is partitioned between ethyl acetate and water. The organic portion is washed with water and brine, dried (sodium sulfate), filtered, and concentrated in vacuo. The residue is chromatographed on SiO2 (5% methanol/dichloromethane) to yield the title compound, 0.41 g (91%), as a white solid.

Workup

  1. customThe mixture is partitioned between ethyl acetate and water
  2. washThe organic portion is washed with water and brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on SiO2 (5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-2b378efd3f46416db23ce81612080f39
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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