1,1,1-Trimethoxybutane → HCID 67203904, compound

HRID 547305Notes

Reaction equation

HRID 547305 reaction equation
[C:1](OC)(OC)(OC)[CH2:2][CH2:3][CH3:4].Cl.N1C=CC=CC=1.[NH2:18][C:19]1[CH:20]=[N:21][C:22]2[C:27]([C:28]=1[NH:29][CH2:30][C:31]([CH3:34])([OH:33])[CH3:32])=[CH:26][CH:25]=[CH:24][CH:23]=2>C(#N)C>[CH2:2]([C:1]1[N:29]([CH2:30][C:31]([CH3:34])([OH:33])[CH3:32])[C:28]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][C:19]=2[N:18]=1)[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1235121,1,1-TrimethoxybutaneHCID 10176127Pyridinium chlorideHCID 149869411-((3-Aminoquinolin-4-yl)amino)-2-methylpropan-2-ol

Product 1

HCID 67203904HCID 67203904, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trimethyl orthobutyrate (1.90 g, 12.7 mmol) and pyridine hydrochloride (0.13 g, 1.2 mmol) were added to a suspension of 1-[(3-aminoquinolin-4-yl)amino]-2-methylpropan-2-ol (prepared as described in Part A of Example 8, approximately 2.7 g, 11.5 mmol) in acetonitrile (60 mL). The reaction mixture was heated at reflux for 45 minutes with a Dean Stark trap, then was allowed to cool to room temperature and was concentrated under reduced pressure. The crude product was subjected to flash chromatography (silica gel, eluted with 5% methanol in dichloromethane) to yield a mixture of compounds that were combined and resubjected to the reaction conditions. The mixture was allowed to cool to room temperature and was concentrated under reduced pressure to afford 1-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol as a white solid that was used in the next step without purification.

Workup

  1. customprepared
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 45 minutes with a Dean Stark trap
  4. concentrationwas concentrated under reduced pressure
  5. washThe crude product was subjected to flash chromatography (silica gel, eluted with 5% methanol in dichloromethane)
  6. customto yield
  7. additiona mixture of compounds that
  8. customresubjected to the reaction conditions
  9. temperatureto cool to room temperature
  10. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-8d3af85930ff4aa399eeaf87e291c1d5
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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