HCID 58833641, compound → HCID 58833655, compound

HRID 540920Notes

Reaction equation

HRID 540920 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:18][O:19][CH2:20][CH3:21])[N:14]([CH2:15][CH2:16][CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:22][CH:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]3)=[CH:5][C:4]=2[N:3]=1>Cl>[CH2:20]([O:19][CH2:18][C:13]1[N:14]([CH2:15][CH2:16][CH3:17])[C:10]2[C:9]3[CH:8]=[CH:7][C:6]([O:22][CH:23]4[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]4)=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=1)[CH3:21]

Participants

3

Reactant 1

HCID 58833641HCID 58833641, compound

Product 1

HCID 58833655HCID 58833655, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
65 °C

Procedure

tert-Butyl 4-{[4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-7-yl]oxy}piperidine-1-carboxylate (2.45 g, 5.07 mmol) was taken up in 4.0M ethanolic hydrogen chloride (15 mL) and heated to 65° C. for 1 hour. The heat was removed and the reaction was allowed to cool to ambient temperature. The ethanol was removed under reduced pressure and the solid residue was dissolved in water (10 mL) and saturated aqueous sodium. chloride (10 mL). The solution was brought to pH 13 with 50% aqueous sodium hydroxide and then extracted with chloroform. The organic fraction was sequentially washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered and evaporated. Trituration with acetonitrile, followed by filtration afforded 1.70 g of 2-(ethoxymethyl)-7-(piperidin-4-yloxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine as a tan solid, mp 202-204° C.

Workup

  1. customThe heat was removed
  2. temperatureto cool to ambient temperature
  3. customThe ethanol was removed under reduced pressure
  4. dissolutionthe solid residue was dissolved in water (10 mL)
  5. extractionextracted with chloroform
  6. washThe organic fraction was sequentially washed with water and saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. filtrationTrituration with acetonitrile, followed by filtration

Sources & evidence

ORD record
ord-a562e7c8d7b6417ca7b8b6a1c61403a1
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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