Trifluoroacetic acid → HCID 22629192, compound

HRID 276959Notes

Reaction equation

HRID 276959 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([N:15]2[C:20](=[O:21])[CH:19]=[CH:18][C:17]([C:22]3[C:23]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[N:24][N:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=34)=[N:16]2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.CO>[O:14]=[C:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]1[N:15]1[C:20](=[O:21])[CH:19]=[CH:18][C:17]([C:22]2[C:23]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[N:24][N:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=23)=[N:16]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22629151HCID 22629151, compound

Product 1

HCID 22629192HCID 22629192, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[2-(1-tert-butoxycarbonyl-4-oxopiperidin-3-yl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (500 mg) in dichloromethane (10 ml) was added trifluoroacetic acid (5 ml) at room temperature, and stirred for 2 hours. Solvent was evaporated and removed by toluene azeotrope to give residue, which was chromatographed on silica gel eluting in turn with 5% and 10% methanol in dichloromethane. Fractions containing desired product were collected and concentrated in vacuo to give residue, which was dissolved in methanol and passed through Amberlite IRA-910 (10ml). eluting with methanol. Solvent was removed under reduced pressure to give 3-[2-(4-oxopiperidin-3-yl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.3 g).

Workup

  1. customSolvent was evaporated
  2. customremoved by toluene azeotrope
  3. customto give residue, which
  4. customwas chromatographed on silica gel eluting in turn with 5% and 10% methanol in dichloromethane
  5. additionFractions containing desired product
  6. customwere collected
  7. concentrationconcentrated in vacuo
  8. customto give residue, which
  9. washeluting with methanol
  10. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-744db13d864142c4a378e1b927557f02
Source dataset
uspto-grants-2002_03
Patent number
US06355640B1

Reaction notes

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