m-Chloroperbenzoic acid → HCID 69506733, compound

HRID 2366723Notes

Reaction equation

HRID 2366723 reaction equation
[CH3:1][C:2]([CH3:23])([CH2:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=[C:10]1[CH3:22])[C:3]([O:5][CH2:6]C)=[O:4].C1C=C(Cl)C=C(C(OO)=O)C=1.ClC(Cl)(Cl)C([N:39]=C=O)=O>C[O-].[Na+]>[NH2:39][C:13]1[C:12]2[N:11]=[C:10]([CH3:22])[N:9]([CH2:8][C:2]([CH3:1])([CH3:23])[C:3]([O:5][CH3:6])=[O:4])[C:21]=2[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:14]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 76400Trichloroacetyl isocyanateHCID 57447114HCID 57447114, compound

Product 1

HCID 69506733HCID 69506733, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

The methods described in Part B of Example 60 were used to treat ethyl 2,2-dimethyl-3-(2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)propanoate (7.2 g, 22 mmol) with mCPBA (9.6 g of 77% pure material), followed by trichloroacetyl isocyanate (3.1 mL, 26 mmol), followed by sodium methoxide (20 mL of 25% in methanol). After the collection of the precipitate, the filtrate was concentrated under reduced pressure, and the residue was mixed with methanol (50 mL). The resulting solid was isolated by filtration, and the isolated solids were combined to provide 2.3 g of methyl 3-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanoate.

Workup

  1. customAfter the collection of the precipitate
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionthe residue was mixed with methanol (50 mL)
  4. customThe resulting solid was isolated by filtration

Sources & evidence

ORD record
ord-69138cbe6f6a4b0f82996b519f8e493b
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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