Hydrochloric Acid → HCID 58833720, compound

HRID 540914Notes

Reaction equation

HRID 540914 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]=[C:7]([O:22][CH:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]3)[CH:6]=[CH:5][C:4]=2[N:3]=1.Cl.O>C(O)C>[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]=[C:7]([O:22][CH:23]4[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]4)[CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=1)[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 58833615HCID 58833615, compound

Product 1

HCID 58833720HCID 58833720, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 4-{[4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl]oxy}piperidine-1-carboxylate (prepared as described in Example 410, 2.9 g, 6.0 mmol) and 4 M ethanolic hydrogen chloride (15 mL) in ethanol (20 mL) was heated at reflux for 2 hours. The solution was allowed to cool to ambient temperature and was concentrated under reduced pressure to approximately 17 mL, causing a solid to form. Water was added to dissolve the solid and the remainder of the ethanol was evaporated under reduced pressure. The aqueous solution was adjusted to approximately pH 13 with 50% aqueous sodium hydroxide, then was extracted with chloroform. 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 product was recrystallization from acetonitrile to yield 1.25 g of 2-(ethoxymethyl)-8-(piperidin-4-yloxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine as off-white needles, mp 176-178° C.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationwas concentrated under reduced pressure to approximately 17 mL
  3. customto form
  4. dissolutionto dissolve the solid
  5. customthe remainder of the ethanol was evaporated under reduced pressure
  6. extractionwas extracted with chloroform
  7. washwashed with water and saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customrecrystallization from acetonitrile

Sources & evidence

ORD record
ord-cae449f2d4e24b38a676eedf9a31f757
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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