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

HRID 2097400Notes

Reaction equation

HRID 2097400 reaction equation
[CH:1]1([O:4][C:5]2[CH:6]=[C:7]([C:15]3[NH:32][C:18]4[CH:19]=[N:20][N:21](COCC[Si](C)(C)C)[C:22](=[O:23])[C:17]=4[C:16]=3[CH2:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:8]=[CH:9][C:10]=2[O:11][CH:12]([F:14])[F:13])[CH2:3][CH2:2]1.C1(OC2C=C(C3NC4C=NN(COCC[Si](C)(C)C)C(=O)C=4C=3CCC)C=CC=2OC(F)F)CC1>>[CH:1]1([O:4][C:5]2[CH:6]=[C:7]([C:15]3[NH:32][C:18]4[CH:19]=[N:20][NH:21][C:22](=[O:23])[C:17]=4[C:16]=3[CH2:33][CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:8]=[CH:9][C:10]=2[O:11][CH:12]([F:13])[F:14])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 1363466672-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-propyl-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 1363466692-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-phenethyl-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 1358450492-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-phenethyl-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 80%

Procedure

Reaction was carried out in the same manner as in Example 6-(c) except for using 364 mg (0.641 mmol) of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-3-phenethyl-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Example 21-(b) in place of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-5-(2-trimethylsilylethoxymethyl)-3-propyl-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one. After completion of the reaction, the solid was collected by filtration from the reaction suspension and washed with 1,4-dioxane. To the obtained solid were added methanol and 28% aqueous ammonia, and the mixture was stirred at room temperature for 16 hours. Then, water was added to the solution, and the precipitated solid was collected by filtration. The obtained solid was washed with water and dried under reduced pressure to obtain 224 mg of the title compound as a white solid. (Yield: 80%)

Workup

  1. customReaction
  2. customAfter completion of the reaction
  3. filtrationthe solid was collected by filtration from the reaction suspension
  4. washwashed with 1,4-dioxane
  5. additionTo the obtained solid were added methanol and 28% aqueous ammonia
  6. additionThen, water was added to the solution
  7. filtrationthe precipitated solid was collected by filtration
  8. washThe obtained solid was washed with water
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-ada525026f704989a123067bb645eac0
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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