2-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one → HCID 135845022, compound

HRID 2097441Notes

Reaction equation

HRID 2097441 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[CH2:33][O:34][CH2:35][CH:36]3[CH2:38][CH2:37]3)[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=NNC(=O)C=4C=3)C=CC=2OC(F)F)CC1>C(OCC)(=O)C>[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[CH2:33][O:34][CH2:35][CH:36]3[CH2:38][CH2:37]3)[CH:8]=[CH:9][C:10]=2[O:11][CH:12]([F:13])[F:14])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 666024612-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 66602845HCID 66602845, compound

Product 1

HCID 135845022HCID 135845022, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Reaction was carried out in the same manner as in Example 1-(b) except for using 581 mg (1.06 mmol) of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-3-cyclopropylmethoxymethyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo-[2,3-d]pyridazin-4-one obtained in Example 59-(a) 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 precipitated solid was collected by filtration and washed with water. The obtained crude solid was applied to silica gel column chromatography (Eluent; ethyl acetate), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 287 mg of the title compound as a white solid. (Yield: 65%)

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. customprecipitated solid
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customThe obtained crude solid

Sources & evidence

ORD record
ord-9bea9cf2e2cc480283b59900c2b87dba
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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