Pyridine → HCID 68753912, compound

HRID 1853427Notes

Reaction equation

HRID 1853427 reaction equation
[CH:1]1([C:4](Cl)=O)[CH2:3][CH2:2]1.[NH2:7][C:8]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11].N1C=CC=CC=1.[NH2:27][NH2:28]>C1COCC1.C(OCC)(=O)C>[NH2:27][N:28]1[C:10](=[O:11])[C:9]2[C:8](=[CH:16][C:15]([C:17]([F:20])([F:19])[F:18])=[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 678694-(Trifluoromethyl)anthranilic acidHCID 77637Cyclopropanecarbonyl chloride

Product 1

HCID 68753912HCID 68753912, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Cyclopropanecarbonyl chloride (2.71 ml, 29.6 mmol) was added to a solution of 2-amino-4-(trifluoromethyl)benzoic acid (2.00 g, 9.75 mmol) in THF (50 mL) followed by pyridine (4.07 ml, 50.3 mmol). The mixture was stirred at 70° C. overnight. The mixture was cooled at 0° C., hydrazine was added, and the reaction was stirred at room temperature for 30 minutes and then at 75° C. for 24 hours. The reaction was cooled at 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 again. The process was repeated to obtain the title compound.

Workup

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

Sources & evidence

ORD record
ord-e03a4f8e53e7447d8f4f6d84a8ba3c32
Source dataset
uspto-grants-2015_02
Patent number
US08962639B2

Reaction notes

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