Ethylenediamine → 2-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097373Notes

Reaction equation

HRID 2097373 reaction equation
[CH:1]1([O:4][C:5]2[CH:6]=[C:7]([C:15]3[N:24](COCC[Si](C)(C)C)[C:18]4[CH:19]=[N:20][NH:21][C:22](=[O:23])[C:17]=4[CH:16]=3)[CH:8]=[CH:9][C:10]=2[O:11][CH:12]([F:14])[F:13])[CH2:3][CH2:2]1.O1CCCC1.C(N)CN.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CCCCCC.O>[CH:1]1([O:4][C:5]2[CH:6]=[C:7]([C:15]3[NH:24][C:18]4[CH:19]=[N:20][NH:21][C:22](=[O:23])[C:17]=4[CH:16]=3)[CH:8]=[CH:9][C:10]=2[O:11][CH:12]([F:13])[F:14])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 3301EthylenediamineHCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 666024612-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 1356204952-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

To 750 mg (1.62 mmol) of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Example 1-(a) were added 2.5 ml of tetrahydrofuran, 0.22 ml of ethylenediamine and 16.5 ml of tetrahydrofuran solution containing 1M tetrabutylammonium fluoride, and the mixture was refluxed for 48 hours. After completion of the reaction, water and hexane were added to the reaction mixture, precipitated solid was collected by filtration, and dried under reduced pressure. The obtained dried material was dissolved in ethanol, poured into water, and precipitated solid was collected by filtration. The obtained solid was washed with water, and dried under reduced pressure to obtain 459 mg of the title compound as a white solid. (Yield: 85%)

Workup

  1. temperaturethe mixture was refluxed for 48 hours
  2. additionwere added to the reaction mixture
  3. customprecipitated solid
  4. filtrationwas collected by filtration
  5. customdried under reduced pressure
  6. dissolutionThe obtained dried material was dissolved in ethanol
  7. additionpoured into water
  8. customprecipitated solid
  9. filtrationwas collected by filtration
  10. washThe obtained solid was washed with water
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-46b09c97f5c84d488205230f3618005e
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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