Ethyl orthopropionate → 4-[(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]tetrahydro-2H-pyran-4-ol

HRID 1469292Notes

Reaction equation

HRID 1469292 reaction equation
C(O[C:4](OCC)(OCC)[CH2:5][CH3:6])C.Cl.N1C=CC=CC=1.[NH2:20][C:21]1[CH:22]=[N:23][C:24]2[C:29]([C:30]=1[NH:31][CH2:32][C:33]1([OH:39])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)=[CH:28][CH:27]=[CH:26][CH:25]=2>C1(C)C=CC=CC=1>[CH2:5]([C:6]1[N:31]([CH2:32][C:33]2([OH:39])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[C:30]2[C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:23]=[CH:22][C:21]=2[N:20]=1)[CH3:4]

Participants

5

Reactant 3

HCID 66995Ethyl orthopropionateHCID 10176127Pyridinium chlorideHCID 574578244-[(3-Aminoquinolin-4-ylamino)methyl]tetrahydropyran-4-ol

Product 1

HCID 575154484-[(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]tetrahydro-2H-pyran-4-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triethylorthopropionate (2.4 mL, 12.0 mmol) and pyridine hydrochloride (60 mg, 0.5 mmol) were added to a suspension of 4-[(3-aminoquinolin-4-ylamino)methyl]tetrahydropyran-4-ol (10.0 mmol) in toluene (50 mL). The reaction mixture was heated at reflux for 2.5 hours and then concentrated under reduced pressure. The residue was triturated with acetonitrile and the filtered to provide 4-[(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]tetrahydro-2H-pyran-4-ol as a tan solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2.5 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with acetonitrile
  5. filtrationthe filtered

Sources & evidence

ORD record
ord-cf1a2d27b1c74e9abbed66035d7cfea5
Source dataset
uspto-grants-2015_04
Patent number
US09006264B2

Reaction notes

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