Pyridine → HCID 68749793, compound

HRID 1912512Notes

Reaction equation

HRID 1912512 reaction equation
[CH:1]1([C:4](Cl)=O)[CH2:3][CH2:2]1.[NH2:7][C:8]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11].N1C=CC=CC=1.[NH2:24][NH2:25]>O1CCCC1.C(OCC)(=O)C>[NH2:24][N:25]1[C:10](=[O:11])[C:9]2[C:8](=[CH:16][C:15]([F:17])=[CH:14][CH:13]=2)[N:7]=[C:4]1[CH:1]1[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 9321HydrazineHCID 77637Cyclopropanecarbonyl chlorideHCID 27249674-Fluoroanthranilic acid

Product 1

HCID 68749793HCID 68749793, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Cyclopropanecarbonyl chloride (3.59 mL, 39.2 mmol) was added to a solution of 2-amino-4-fluorobenzoic acid (Aldrich) (2.0 g, 12.9 mmol) and pyridine (5.38 mL, 66.5 mmol) in tetrahydrofuran (15 mL). The mixture was stirred at 70° C. overnight. The mixture was cooled at 0° C., hydrazine (4.86 mL, 155 mmol) was added and the reaction was stirred at about room temperature for 30 minutes, then at about 75° C. for 24 hours. The reaction mixture was cooled to about 22° C., diluted with ethyl acetate, washed with aq. NaHCO3, dried with magnesium sulfate, filtered, and concentrated. The residue was suspended in toluene and concentrated. The process was repeated to obtain the crude title compound.

Workup

  1. temperatureThe mixture was cooled at 0° C.
  2. stirringthe reaction was stirred at about room temperature for 30 minutes
  3. waitat about 75° C. for 24 hours
  4. temperatureThe reaction mixture was cooled to about 22° C.
  5. washwashed with aq. NaHCO3
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-40d11562a460487cb32227b09b47f8a1
Source dataset
uspto-grants-2013_12
Patent number
US08609674B2

Reaction notes

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