1,1,1-Trimethoxypropane → HCID 86626166, compound

HRID 598328Notes

Reaction equation

HRID 598328 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:9][CH:8]=[C:7]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:6]=2.Cl.N1C=C[CH:37]=[CH:36][CH:35]=1.C(OC)(OC)(OC)CC>C1(C)C=CC=CC=1>[CH2:26]([O:25][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:35]([CH2:36][CH3:37])=[N:1][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 1411451,1,1-TrimethoxypropaneHCID 10176127Pyridinium chlorideHCID 68900070Tert-butyl [4-(3-amino-7-benzyloxyquinolin-4-ylamino)butyl]carbamate

Product 1

HCID 86626166HCID 86626166, compoundYield 206.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl [4-(3-amino-7-benzyloxyquinolin-4-ylamino)butyl]carbamate (20.7 g, 43.6 mmol) was dissolved in toluene (225 mL). Pyridine hydrochloride (2.03 g) and trimethyl orthopropionate (6.2 mL, 43.6 mmol) were added, and the mixture was heated at reflux for 3.25 hours. The reaction was allowed to cool to room temperature; a fine precipitate formed. The precipitate was isolated by filtration and washed with toluene. The off-white solid was allowed to dry for 2 hours under vacuum. The filtrate was evaporated, and the residue was dissolved in dichloromethane. The resulting solution was washed with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford a brown amorphous solid. The solids were combined to provide 17.2 g of tert-butyl [4-(7-benzyloxy-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3.25 hours
  3. customa fine precipitate formed
  4. customThe precipitate was isolated by filtration
  5. washwashed with toluene
  6. customto dry for 2 hours under vacuum
  7. customThe filtrate was evaporated
  8. dissolutionthe residue was dissolved in dichloromethane
  9. washThe resulting solution was washed with water and brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customto afford a brown amorphous solid

Sources & evidence

ORD record
ord-dc39a792b84f4efdb78e0499feab7275
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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