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

HRID 2097392Notes

Reaction equation

HRID 2097392 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[C:16]=3[C:33]#[C:34][Si](CC)(CC)CC)[CH:8]=[CH:9][C:10]=2[O:11][CH:12]([F:14])[F:13])[CH2:3][CH2:2]1.C1(OC2C=C(C3N(COCC[Si](C)(C)C)C4C=NN(COCC[Si](C)(C)C)C(=O)C=4C=3C)C=CC=2OC(F)F)CC1>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[C:16]=3[C:33]#[CH:34])[CH:8]=[CH:9][C:10]=2[O:11][CH:12]([F:13])[F:14])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 666024312-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-triethylsilylethynyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 666028152-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-methyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 1358450282-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-ethynyl-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 52.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reaction was carried out in the same manner as in Example 4-(b) except for using 32 mg (0.053 mmol) of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-3-triethylsilylethynyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Example 16-(a) in place of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-3-methyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer after separation was washed successively with water and then with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. To the obtained concentrate were added methanol and water, and the mixture was subjected to ultrasonic wave treatment and the precipitated solid was collected by filtration. The obtained solid was washed successively with water and then with diethyl ether and dried under reduced pressure to obtain 10 mg of the title compound as a beige solid. (Yield: 51%)

Workup

  1. customReaction
  2. additionwas added to the reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic layer after separation
  5. washwas washed successively with water
  6. dry with materialwith a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. concentrationTo the obtained concentrate
  9. additionwere added methanol and water
  10. filtrationthe precipitated solid was collected by filtration
  11. washThe obtained solid was washed successively with water
  12. dry with materialwith diethyl ether and dried under reduced pressure

Sources & evidence

ORD record
ord-ebd6e35d826146b89e75ac102321fff0
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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