Ammonia → HCID 135620468, compound

HRID 2097425Notes

Reaction equation

HRID 2097425 reaction equation
ClCCl.[Br:4][C:5]1[C:13]2[C:12](=[O:14])[NH:11][N:10]=[CH:9][C:8]=2[N:7](COCC[Si](C)(C)C)[C:6]=1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH:32]2[CH2:34][CH2:33]2)[CH:24]=1.Cl.N>CO.O1CCOCC1>[Br:4][C:5]1[C:13]2[C:12](=[O:14])[NH:11][N:10]=[CH:9][C:8]=2[NH:7][C:6]=1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH:32]2[CH2:33][CH2:34]2)[CH:24]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 66602481HCID 66602481, compound

Product 1

HCID 135620468HCID 135620468, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To 1 ml of dichloromethane solution containing 186 mg (0.367 mmol) of 3-bromo-2-(3-cyclopropoxy-4-methoxyphenyl)-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]-pyridazin-4-one obtained in Example 43-(a) was added 6 ml of 1,4-dioxane solution containing 4N hydrogen chloride, and the mixture was stirred at room temperature for 8 hours. After completion of the reaction, the solid obtained from the reaction suspension by filtration was washed with diisopropyl ether. To the obtained crude solid were added methanol and 28% aqueous ammonia, and the mixture was stirred at room temperature for 5 hours. Then, the solution was concentrated under reduced pressure and the obtained solid was washed with ethyl acetate and dried under reduced pressure to obtain 85 mg of the title compound as a white solid. (Yield: 62%)

Workup

  1. customAfter completion of the reaction
  2. customthe solid obtained from the reaction suspension by filtration
  3. washwas washed with diisopropyl ether
  4. customTo the obtained crude solid
  5. stirringthe mixture was stirred at room temperature for 5 hours
  6. concentrationThen, the solution was concentrated under reduced pressure
  7. washthe obtained solid was washed with ethyl acetate
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-e3eff324dda44e85bee6865e4fc932b5
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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