m-Chloroperbenzoic acid → HCID 69506712, compound

HRID 2366725Notes

Reaction equation

HRID 2366725 reaction equation
[N:1]1([CH2:14][C:15]([CH3:22])([CH3:21])[C:16]([O:18][CH2:19]C)=[O:17])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.C1C=C(Cl)C=C(C(OO)=O)C=1.ClC(Cl)(Cl)C([N:38]=C=O)=O.[N-]=C=O.C[O-].[Na+]>>[NH2:38][C:5]1[C:4]2[N:3]=[CH:2][N:1]([CH2:14][C:15]([CH3:22])([CH3:21])[C:16]([O:18][CH3:19])=[O:17])[C:13]=2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]=1

Participants

6

Reactant 5

HCID 70297m-Chloroperbenzoic acidHCID 76400Trichloroacetyl isocyanate2×HCID 105034IsocyanateHCID 10942334Sodium MethoxideHCID 57447115HCID 57447115, compound

Product 1

HCID 69506712HCID 69506712, compoundYield 38.5%

Conditions

Temperature
0 °C

Procedure

A modification of the methods described in Part B of Example 60 was used to treat ethyl 3-(1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanoate (4.3 g, 14 mmol) with mCPBA (6.3 g of 77% pure material), followed by trichloroacetyl isocyanate (2.0 mL, 17 mmol). The reaction with the isocyanate was stirred for two hours before the addition of additional trichloroacetyl isocyanate (1.0 mL) and stirring for an additional two hours. After the reaction with sodium methoxide (11 mL of 25% in methanol), the solvent was removed under reduced pressure. The residue was mixed with methanol (25 mL), and the mixture was cooled to 0° C. and filtered to isolate 1.61 g of methyl 3-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanoate as a solid. The filtrate was concentrated under reduced pressure, and the residue was mixed with saturated aqueous sodium bicarbonate (100 mL). A precipitate formed, was isolated by filtration, and was mixed with concentrated hydrochloric acid to adjust to pH 7. The precipitate was again isolated by filtration and dissolved in dichloromethane. The resulting solution was dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide an additional 1.51 g of methyl 3-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanoate as an oil.

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionThe residue was mixed with methanol (25 mL)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-228d0061b48a44ce82c3c7340d891e63
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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