Trimethyl orthoformate → HCID 57447115, compound

HRID 2366724Notes

Reaction equation

HRID 2366724 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([CH3:21])([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH:22](OC)(OC)OC.C(OC)(OC)(OC)CCC.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>>[N:12]1([CH2:13][C:14]([CH3:20])([CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[CH:22]1

Participants

5

Reactant 4

HCID 9005Trimethyl orthoformate2×HCID 1235121,1,1-TrimethoxybutaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57447056HCID 57447056, compound

Product 1

HCID 57447115HCID 57447115, compound

Procedure

Ethyl 3-(3-aminoquinolin-4-ylamino)-2,2-dimethylpropanoate (see Example 26 Parts A through D, 5.3 g, 18 mmol) was treated according to a modification of the method described in Part B of Example 8 using trimethyl orthoformate in lieu of trimethyl orthobutyrate. Prior to the addition of trimethyl orthoformate (3.0 mL, 27 mmol) and pyridinium p-toluenesulfonate (0.050 g), the reaction was heated at reflux for 15 minutes. The reaction was heated at reflux overnight, allowed to cool to ambient temperature, washed with saturated aqueous sodium bicarbonate (2×35 mL), and extracted with water (45 mL) containing 10% hydrochloric acid (5 mL). The acidic extract was made basic with the addition of potassium carbonate and then extracted with dichloromethane (3×50 mL). The combined organic extracts were dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 4.3 g of ethyl 3-(1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanoate as an oil.

Workup

  1. additionwas treated
  2. temperaturethe reaction was heated
  3. temperatureat reflux for 15 minutes
  4. temperatureThe reaction was heated
  5. temperatureat reflux overnight
  6. washwashed with saturated aqueous sodium bicarbonate (2×35 mL)
  7. extractionextracted with water (45 mL)
  8. additioncontaining 10% hydrochloric acid (5 mL)
  9. extractionThe acidic extract
  10. additionwas made basic with the addition of potassium carbonate
  11. extractionextracted with dichloromethane (3×50 mL)
  12. dry with materialThe combined organic extracts were dried over potassium carbonate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5776b56ec32c4cd3941e645020e0f270
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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