Tetrahydrofuran → HCID 178455216, compound

HRID 415486Notes

Reaction equation

HRID 415486 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[Si:13]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=[C:28]([Cl:36])[C:27]=1[NH2:37])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C1COCC1>N1C=CC=CC=1>[Si:13]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[C:26]2[C:35]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[N:29]=[C:28]([Cl:36])[C:27]=2[N:37]=[C:1]1[OH:2])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 86633735HCID 86633735, compound

Product 1

HCID 178455216HCID 178455216, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

1,1′-Carbonyldiimidazole (32.6 g, 201 mmol) was added to a solution of N4-[4-(tert-butyldimethylsilanyloxy)butyl]-2-chloroquinoline-3,4-diamine (50.96 g, 134.1 mmol), THF (250 mL), and pyridine (250 mL), and the reaction was heated at 80° C. overnight and allowed to cool. The volatiles were removed under reduced pressure. The residue was dissolved in ethyl acetate (600 mL), and the resulting solution was washed sequentially with brine (2×400 mL) and water (2×400 mL) and then concentrated under reduced pressure. The resulting solid was triturated with diethyl ether (1 L), collected by filtration, washed with diethyl ether (800 mL), and dried under vacuum for 30 minutes to provide 28.39 g of 1-[4-(tert-butyldimethylsilanyloxy)butyl]-4-chloro-1H-imidazo[4,5-c]quinolin-2-ol as a white solid.

Workup

  1. temperatureto cool
  2. customThe volatiles were removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (600 mL)
  4. washthe resulting solution was washed sequentially with brine (2×400 mL) and water (2×400 mL)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting solid was triturated with diethyl ether (1 L)
  7. filtrationcollected by filtration
  8. washwashed with diethyl ether (800 mL)
  9. customdried under vacuum for 30 minutes

Sources & evidence

ORD record
ord-99d6db9956514dc59e779aefa9ad81ab
Source dataset
uspto-grants-2012_01
Patent number
US08088790B2

Reaction notes

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