Pyridine → HCID 89662143, compound

HRID 1774523Notes

Reaction equation

HRID 1774523 reaction equation
[CH3:1][N:2]([CH3:19])[C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[N:6]=[C:5]([C:16]([NH2:18])=O)[CH:4]=1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[CH3:1][N:2]([CH3:19])[C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[N:6]=[C:5]([C:16]#[N:18])[CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 89662188HCID 89662188, compound

Product 1

HCID 89662143HCID 89662143, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.33 g of 5-(dimethylamino)-1-(2-fluorobenzyl)-1H-pyrazole-3-carboxamide 1-10-1 (5.07 mmol, 1.0 eq.) were dissolved in 74 mL of dry THF. 1.03 mL of pyridine (12.7 mmol, 2.50 eq.) were added. Then 1.79 mL of trifluoroacetic anhydride (12.7 mmol, 2.50 eq.) were added dropwise. The reaction mixture was stirred for 24 hours at rt. Then the reaction mixture was partitioned between water and ethyl acetate. The separated aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (hexane/ethyl acetate) to provide 406 mg (1.66 mmol, 33%) of analytically pure target compound.

Workup

  1. customThen the reaction mixture was partitioned between water and ethyl acetate
  2. extractionThe separated aqueous layer was extracted twice with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (hexane/ethyl acetate)
  6. customto provide 406 mg (1.66 mmol, 33%) of analytically pure target compound

Sources & evidence

ORD record
ord-2a2128969c654c479a1b8044928ae07d
Source dataset
uspto-grants-2016_02
Patent number
US09260412B2

Reaction notes

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