Sodium Carbonate → HCID 58833615, compound

HRID 540913Notes

Reaction equation

HRID 540913 reaction equation
ClC(Cl)(Cl)C([N:5]=C=O)=O.[CH2:10]([O:12][CH2:13][C:14]1[N:15]([CH2:42][CH2:43][CH3:44])[C:16]2[C:25]3[CH:24]=[C:23]([O:26][CH:27]4[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]4)[CH:22]=[CH:21][C:20]=3[N+:19]([O-])=[CH:18][C:17]=2[N:41]=1)[CH3:11].[OH-].[NH4+].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[NH2:5][C:18]1[C:17]2[N:41]=[C:14]([CH2:13][O:12][CH2:10][CH3:11])[N:15]([CH2:42][CH2:43][CH3:44])[C:16]=2[C:25]2[CH:24]=[C:23]([O:26][CH:27]3[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]3)[CH:22]=[CH:21][C:20]=2[N:19]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 14923Ammonium HydroxideHCID 76400Trichloroacetyl isocyanateHCID 68969451HCID 68969451, compound

Product 1

HCID 58833615HCID 58833615, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Trichloroacetyl isocyanate (1.22 mL, 10.2 mmol) was added dropwise a stirred solution of tert-butyl 4-{[2-(ethoxymethyl)-5-oxido-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl]oxy}piperidine-1-carboxylate (4.5 g, 9.29 mmol) in dichloromethane (90 mL) at room temperature. After 1.5 hours, ammonium hydroxide (4.5 mL) was added and the mixture was allowed to stir for 1 hour. Saturated aqueous sodium carbonate (60 mL) and water (20 mL) were added to the mixture. After 30 minutes, the mixture was transferred to a separatory funnel and the layers were separated. The aqueous layer was extracted with chloroform (2×100 mL). The organic layers were combined, washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 1-25% CMA in chloroform) followed by recrystallization from acetonitrile to yield 2.3 g of tert-butyl 4-{[4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl]oxy}piperidine-1-carboxylate as a gray solid, mp 179.5-181° C.

Workup

  1. waitAfter 30 minutes
  2. customthe mixture was transferred to a separatory funnel
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with chloroform (2×100 mL)
  5. washwashed with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 1-25% CMA in chloroform)
  10. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-c412374a327f4225a4a3fa736fe2ca85
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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