Hydrochloric Acid → HCID 59751944, compound

HRID 749098Notes

Reaction equation

HRID 749098 reaction equation
[C:1]1([C:7]2[C:12]3[N:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:10](=[O:17])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=C2C(=O)OC(=O)C=12.C1([Mg]Cl)C=CC=CC=1.Cl>[Pt](=O)=O.CN(C)C=O>[C:1]1([C:7]2[C:12]3[NH:13][CH2:14][CH2:15][CH2:16][C:11]=3[C:10](=[O:17])[NH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 10561040HCID 10561040, compoundHCID 178478979HCID 178478979, compound

Product 1

HCID 59751944HCID 59751944, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6228DimethylformamideSolvent

Procedure

Under an atmosphere of hydrogen, a mixture of 8-phenylpyrido[2,3-d]pyridazin-5(6H)-one (100 mg; It was prepared by the same procedure as described in Reference example 1→Example 1 using furo[3,4-b]pyridine-5,7-dione instead of 4,5,6,7-tetrahydro-2-benzofuran-1,3-dione, and phenylmagnesium chloride instead of 3-(bis(trimethylsilyl)amino)phenylmagnesium chloride), platinum(IV)oxide (10 mg), 1N hydrochloric acid (0.5 mL) and dimethylformamide (5 mL) was stirred at room temperature for 6 hours. The reaction mixture was filtrated through Celite. The filtrate was concentrated. The residue was diluted with ethyl acetate. The diluted solution was washed with a saturated aqueous sodium hydrogen carbonate solution and brine sequentially, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from ethanol to give the compound of the present invention (42 mg) having the following physical data. Moreover, the compound was converted to a corresponding salt thereof by conventional method.

Workup

  1. customIt was prepared by the same procedure
  2. filtrationThe reaction mixture was filtrated through Celite
  3. concentrationThe filtrate was concentrated
  4. additionThe residue was diluted with ethyl acetate
  5. washThe diluted solution was washed with a saturated aqueous sodium hydrogen carbonate solution and brine sequentially
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethanol
  9. customto give the compound of the present invention (42 mg)

Sources & evidence

ORD record
ord-27d31dad1300439d941b74e496e34a6c
Source dataset
uspto-grants-2008_07
Patent number
US07402580B2

Reaction notes

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