HCID 86611634, compound → HCID 68933059, compound

HRID 521295Notes

Reaction equation

HRID 521295 reaction equation
CON(C)[C:4](=[O:24])[CH2:5][CH2:6][CH2:7][N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:10]=[C:9]1[CH2:21][CH2:22][CH3:23].[CH2:26]([Mg]Cl)[CH:27]([CH3:29])[CH3:28]>C1COCC1.C(OCC)C>[CH3:26][CH:27]([CH3:29])[CH2:28][C:4](=[O:24])[CH2:5][CH2:6][CH2:7][N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:10]=[C:9]1[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 2

HCID 86611634HCID 86611634, compoundHCID 178418368HCID 178418368, compound

Product 1

HCID 68933059HCID 68933059, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-methoxy-N-methyl-4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyramide (4.80 g, 14.1 mmol) in THF (100 mL) in a dry ice/isopropanol bath was added a solution of isobutylmagnesium chloride (28 mL of a 2 M solution in diethyl ether, 56 mmol) over a period of several minutes. When addition was complete, the reaction flask was removed from the cold bath and the mixture stirred for 4 hours at room temperature. A 10% solution of hydrochloric acid in water (3 mL) was added slowly, followed by a saturated solution of sodium bicarbonate in water (15 mL) and dichloromethane (100 mL). The layers were separated, the aqueous phase extracted with dichloromethane (1×75 mL), and the combined organics dried over potassium carbonate, filtered, and concentrated under reduced pressure. After chromatography on silica gel (elution with 5% methanol in dichloromethane) 6-methyl-1-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)heptan-4-one (2.40 g) was obtained as an oil.

Workup

  1. additionWhen addition
  2. customthe reaction flask was removed from the cold bath
  3. additionA 10% solution of hydrochloric acid in water (3 mL) was added slowly
  4. customThe layers were separated
  5. extractionthe aqueous phase extracted with dichloromethane (1×75 mL)
  6. dry with materialthe combined organics dried over potassium carbonate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0be20439a94547afad21d8fe8ee8adef
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

Loading…