Pyridine → [7-Benzyloxy-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

HRID 2383170Notes

Reaction equation

HRID 2383170 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]([CH3:17])([OH:16])[CH3:15])=[CH:9][CH:8]=[C:7]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:6]=2.N1C=CC=CC=1.[CH3:32][O:33][CH2:34][CH2:35][C:36](Cl)=O>C1(C)C=CC=CC=1>[CH2:19]([O:18][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]([CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])[C:36]([CH2:35][CH2:34][O:33][CH3:32])=[N:1][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27597283-Methoxypropanoyl chlorideHCID 67050960HCID 67050960, compound

Product 1

HCID 67051129[7-Benzyloxy-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-olYield 75.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(3-Amino-7-benzyloxyquinolin-4-ylamino)-2-methyl-propan-2-ol (25 g, 74.09 mmol) was added to 500 mL of pyridine. To this mixture was added in a dropwise manner a solution of methoxypropionyl chloride (10 g, 81.5 mmol) dissolved in 20 mL of toluene. After approximately half of the acid chloride had been added, the reaction mixture became completely homogenous. Two hours after the addition of the acid chloride, the reaction mixture was heated to reflux and maintained overnight. The solvent was concentrated through the use of a Dean-Stark trap. Cooling to ambient temperature provided a white precipitate, which was collected by filtration. The solid was slurried in 1 L of 1% hot aqueous sodium carbonate (75-80° C.) for 1 hour. The mixture was then cooled in an ice bath and the solid material was filtered, rinsed with water, and dried to yield 22.7 g of 1-[7-benzyloxy-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as a white solid, mp 170-171.5° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux
  3. temperaturemaintained overnight
  4. concentrationThe solvent was concentrated through the use of a Dean-Stark trap
  5. customprovided a white precipitate, which
  6. filtrationwas collected by filtration
  7. temperatureThe mixture was then cooled in an ice bath
  8. filtrationthe solid material was filtered
  9. washrinsed with water
  10. customdried

Sources & evidence

ORD record
ord-a6ed390e7d6949a5812e849cba1025ed
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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