Hydrochloric Acid → N-Ethyl-N'-[3-(3-fluorophenyl)-1H-5-indazolyl]urea

HRID 503150Notes

Reaction equation

HRID 503150 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](C(OC(C)(C)C)=O)[N:6]=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=1.[CH2:25]([N:27]=[C:28]=[O:29])[CH3:26].Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:25]([NH:27][C:28]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=1)=[O:29])[CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 516892Sodium BicarbonateHCID 222606241h-Indazole-1-carboxylic acid,5-amino-3-(3-fluorophenyl)-,1,1-dimethylethyl ester

Product 1

HCID 23589670N-Ethyl-N'-[3-(3-fluorophenyl)-1H-5-indazolyl]urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 50 mg of tert-butyl 5-amino-3-(3-fluorophenyl)-1H-1-indazolecarboxylate produced in Production Example I-26 in 5 ml tetrahydrofuran was added 0.015 ml of ethyl isocyanate, and the mixture was stirred at room temperature for 2 hours. After the completion of the reaction, to the reaction mixture was added with 1 ml of 5 N hydrochloric acid and the mixture was stirred for further 1 hour. To the reaction mixture was added an aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The extract was sequentially washed with water, dried over anhydrous magnesium sulfate and the solvent was evaporated. To the residue was added diisopropyl ether, and the mixture was filtered, to give 28 mg of the title compound as a colorless powder.

Workup

  1. customAfter the completion of the reaction
  2. stirringthe mixture was stirred for further 1 hour
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was sequentially washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. additionTo the residue was added diisopropyl ether
  8. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-d4d261a1bafe4c73804764024e3bf5e4
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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