Pyridine → HCID 23086661, compound

HRID 229733Notes

Reaction equation

HRID 229733 reaction equation
N1C=CC=CC=1.[CH3:7][C:8]1[CH:9]=[C:10]([OH:28])[C:11]2[CH:12]=[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[N:14]=[N:15][C:16]=2[CH:17]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>CCCCCC.C(OCC)(=O)C>[C:29]([O:28][C:10]1[CH:9]=[C:8]([CH3:7])[CH:17]=[C:16]2[C:11]=1[CH:12]=[C:13]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=1)[N:14]=[N:15]2)(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 1354580247-Methyl-3-(3-trifluoromethylphenyl)cinnolin-5-ol

Product 1

HCID 23086661HCID 23086661, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a pyridine solution (2 mL) of 7-methyl-3-(3-trifluoromethylphenyl)cinnolin-5-ol (60 mg, 0.2 mmol) obtained in Example 70 was added acetic anhydride (3 mL), followed by reaction at room temperature over night. The reaction liquid was concentrated under reduced pressure, followed by adding distilled water (1 mL), extraction with ethyl acetate and purification of residue obtained after concentration of an organic layer under reduced pressure, with HPLC column chromatography (hexane/ethyl acetate=3/1) to obtain an objective compound (25 mg, 36%) as pale yellow solid.

Workup

  1. customfollowed by reaction at room temperature over night
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. additionby adding
  5. distillationdistilled
  6. extractionwater (1 mL), extraction
  7. customwith ethyl acetate and purification of residue
  8. customobtained after concentration of an organic layer under reduced pressure

Sources & evidence

ORD record
ord-243ecda653724554bc1d7723a9b3e920
Source dataset
uspto-grants-2009_07
Patent number
US07563893B2

Reaction notes

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