Trimethyl orthovalerate → 4-[(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]tetrahydro-2H-pyran-4-ol

HRID 44749

Reaction equation

HRID 44749 reaction equation
CO[C:3](OC)(OC)[CH2:4][CH2:5][CH2:6][CH3:7].Cl.N1C=CC=CC=1.[NH2:19][C:20]1[CH:21]=[N:22][C:23]2[C:28]([C:29]=1[NH:30][CH2:31][C:32]1([OH:38])[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1)=[CH:27][CH:26]=[CH:25][CH:24]=2>C1(C)C=CC=CC=1>[CH2:4]([C:3]1[N:30]([CH2:31][C:32]2([OH:38])[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[C:29]2[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N:22]=[CH:21][C:20]=2[N:19]=1)[CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 83755Trimethyl orthovalerateHCID 10176127Pyridinium chlorideHCID 574578244-[(3-Aminoquinolin-4-ylamino)methyl]tetrahydropyran-4-ol

Product 1

HCID 575154444-[(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]tetrahydro-2H-pyran-4-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trimethylorthovalerate (1.8 mL, 10.4 mmol) and pyridine hydrochloride (92 mg, 0.8 mmol) were added to a suspension of 4-[(3-aminoquinolin-4-ylamino)methyl]tetrahydropyran-4-ol (8.0 mmol) in toluene (40 mL). The reaction mixture was heated at reflux for 2.5 hours and then cooled to ambient temperature. A precipitate was isolated by filtration and dried to provide 4-[(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]tetrahydro-2H-pyran-4-ol as a white solid, mp 180-181° C. MS (ESI) m/z 340 (M+H)+; Anal. calcd for C20H25N3O2: C, 70.77; H, 7.42; N, 12.38. Found: C, 70.58; H, 7.53; N, 12.40.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2.5 hours
  3. customA precipitate was isolated by filtration
  4. customdried

Sources & evidence

ORD record
ord-03cbea450e964af3a7ec7dbb0fcdfc4f
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Linked notes

Loading…