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

HRID 2097415Notes

Reaction equation

HRID 2097415 reaction equation
[CH:1]1([O:5][C:6]2[CH:7]=[C:8]([C:16]3[N:25](COCC[Si](C)(C)C)[C:19]4[CH:20]=[N:21][NH:22][C:23](=[O:24])[C:18]=4[C:17]=3[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:9]=[CH:10][C:11]=2[O:12][CH:13]([F:15])[F:14])[CH2:4][CH2:3][CH2:2]1.C1(OC2C=C(C3N(COCC[Si](C)(C)C)C4C=NNC(=O)C=4C=3)C=CC=2OC(F)F)CC1>>[CH:1]1([O:5][C:6]2[CH:7]=[C:8]([C:16]3[NH:25][C:19]4[CH:20]=[N:21][NH:22][C:23](=[O:24])[C:18]=4[C:17]=3[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:9]=[CH:10][C:11]=2[O:12][CH:13]([F:14])[F:15])[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 666024612-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 666027132-(3-Cyclobutoxy-4-difluoromethoxyphenyl)-3-phenyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 1356204662-(3-Cyclobutoxy-4-difluoromethoxyphenyl)-3-phenyl-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 84.2%

Procedure

Reaction was carried out in the same manner as in Example 1-(b) except for using 145 mg (0.261 mmol) of 2-(3-cyclobutoxy-4-difluoromethoxyphenyl)-3-phenyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Example 34-(b) in place of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, water was added to the obtained concentrate, and the mixture was extracted with ethyl acetate. The organic layer after separation was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained solid was dissolved by adding ethyl acetate, followed by addition of diisopropyl ether and hexane, and the precipitated solid was collected by filtration. The obtained solid was dried under reduced pressure to obtain 93 mg of the title compound as a beige solid. (Yield: 84%)

Workup

  1. customReaction
  2. customAfter completion of the reaction
  3. concentrationthe reaction mixture was concentrated under reduced pressure, water
  4. additionwas added to the obtained
  5. concentrationconcentrate
  6. extractionthe mixture was extracted with ethyl acetate
  7. customThe organic layer after separation
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. dissolutionThe obtained solid was dissolved
  11. additionby adding ethyl acetate
  12. additionfollowed by addition of diisopropyl ether and hexane
  13. filtrationthe precipitated solid was collected by filtration
  14. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-3fdf69c4d0f0499ba586407e95f4233a
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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