3-Furanol, tetrahydro- → 1-(2-methylpropyl)-2-propyl-7-(tetrahydrofuran-3-yloxy)-1H-imidazo[4,5-c]quinoline

HRID 2203543Notes

Reaction equation

HRID 2203543 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][O:4][CH2:3]1.[CH3:7][CH:8]([CH3:27])[CH2:9][N:10]1[C:22]2[C:21]3[CH:20]=[CH:19][C:18](O)=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:12]=[C:11]1[CH2:24][CH2:25][CH3:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:7][CH:8]([CH3:27])[CH2:9][N:10]1[C:22]2[C:21]3[CH:20]=[CH:19][C:18]([O:1][CH:2]4[CH2:6][CH2:5][O:4][CH2:3]4)=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:12]=[C:11]1[CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 99603-Furanol, tetrahydro-HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 1363405361-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-ol

Product 1

HCID 689700041-(2-methylpropyl)-2-propyl-7-(tetrahydrofuran-3-yloxy)-1H-imidazo[4,5-c]quinolineYield 88.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Hydroxytetrahydrofuran (0.375 mL, 4.64 mmol) was added to a suspension of 1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-ol (1.0 g, 3.5 mmol) and triphenylphosphine (1.5 g, 5.7 mmol) in THF. Diisopropyl azodicarboxylate (1.1 mL, 5.6 mmol) was added dropwise over a period of three minutes, and the reaction was stirred for 48 hours. The solvent was removed under reduced pressure, the residue was purified by column chromatography on silica gel (eluting with 98:2 dichloromethane:methanol) to provide 1.1 g of 1-(2-methylpropyl)-2-propyl-7-(tetrahydrofuran-3-yloxy)-1H-imidazo[4,5-c]quinoline as an off-white, crystalline solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel (eluting with 98:2 dichloromethane:methanol)

Sources & evidence

ORD record
ord-f592239c12894e4180dcc83f25c38c06
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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