Pyridine → HCID 66855547, compound

HRID 2282199Notes

Reaction equation

HRID 2282199 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]2[N:15]=[C:16]([CH3:21])[C:17]([C:18]([NH2:20])=O)=[C:11]2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(N(CC)CC)C>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]2[N:15]=[C:16]([CH3:21])[C:17]([C:18]#[N:20])=[C:11]2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydride2×HCID 66857189HCID 66857189, compound

Product 1

HCID 66855547HCID 66855547, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 5-(benzyloxy)-2-methylpyrazolo[1,5-a]pyridine-3-carboxamide (1.3 g, 4.8 mmol) produced above, pyridine (1.2 mL, 14 mmol) and tetrahydrofuran (20 mL) was added dropwise under ice-cooling a solution of trifluoroacetic anhydride (1.0 mL, 7.2 mmol) in tetrahydrofuran (2 mL), and the mixture was stirred under ice-cooling for 0.5 hr. Triethylamine (2.0 mL, 14 mmol) was added, and the mixture was stirred at room temperature for 0.5 hr. Trifluoroacetic anhydride (1.0 mL, 7.2 mmol) was added dropwise at room temperature, and the mixture was stirred at room temperature for 0.5 hr and concentrated under reduced pressure. Aqueous sodium bicarbonate solution was added to the obtained residue, and the mixture was extracted with ethyl acetate. The collected organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→100/0). The obtained solution was concentrated under reduced pressure, and the obtained residue was washed with diisopropyl ether/hexane to give the title compound (1.0 g, 79%) as a colorless solid.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling for 0.5 hr
  3. stirringthe mixture was stirred at room temperature for 0.5 hr
  4. stirringthe mixture was stirred at room temperature for 0.5 hr
  5. concentrationconcentrated under reduced pressure
  6. additionAqueous sodium bicarbonate solution was added to the obtained residue
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe collected organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationthe insoluble material was filtered off
  11. concentrationThe filtrate was concentrated under reduced pressure
  12. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→100/0)
  13. concentrationThe obtained solution was concentrated under reduced pressure
  14. washthe obtained residue was washed with diisopropyl ether/hexane

Sources & evidence

ORD record
ord-caf3579d2bf5406194946d88326f75c8
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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