Trifluoroacetic acid → HCID 15522349, compound

HRID 276938Notes

Reaction equation

HRID 276938 reaction equation
C([O:5][C:6]([CH2:8][C:9]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]=1[N:16]1[C:21](=[O:22])[CH:20]=[CH:19][C:18]([C:23]2[C:24]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[N:25][N:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=23)=[N:17]1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:6]([CH2:8][C:9]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]=1[N:16]1[C:21](=[O:22])[CH:20]=[CH:19][C:18]([C:23]2[C:24]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[N:25][N:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=23)=[N:17]1)([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22629250HCID 22629250, compound

Product 1

HCID 15522349HCID 15522349, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[2-(2-t-butoxycarbonylmethyl-1-cycloheptenyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.15 g) in dry dichloromethane (0.5 ml) at room temperature was added trifluoroacetic acid (0.46 ml). After stirring for one day at room temperature, the solution was partitioned between ethyl acetate and a saturated aqueous sodium bicarbonate. The separated aqueous layer was acidified with 1N-hydrochloric acid to pH 3 and extracted with ethyl acetate. The separated organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was recrystallized from ethanol—water to give 3-[2-(2-carboxymethyl-1-cycloheptenyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]-pyridine (0.083 g).

Workup

  1. customthe solution was partitioned between ethyl acetate
  2. extractionextracted with ethyl acetate
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from ethanol—water

Sources & evidence

ORD record
ord-48a73ba58731427f9193cb7f09e32883
Source dataset
uspto-grants-2002_03
Patent number
US06355640B1

Reaction notes

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