Hydrochloric Acid → HCID 68972633, compound

HRID 540891Notes

Reaction equation

HRID 540891 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:18][CH2:19][O: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>C(O)C>[CH3:21][O:20][CH2:19][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

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58833631HCID 58833631, compound

Product 1

HCID 68972633HCID 68972633, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl 4-{[4-amino-2-(2-methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-7-yl]oxy}piperidine-1-carboxylate (prepared as described in Example 387, 2.11 g, 4.36 mmol) was treated with concentrated hydrochloric acid (3 mL). After vigorous bubbling, a solution formed. The solution was diluted with ethanol (50 mL) and evaporated (3×). The resulting oil was dissolved in brine (15 mL) and water (5 mL) and made basic with 50% aqueous sodium hydroxide (approximately 1.5 mL). The aqueous layer was extracted with dichloromethane (3×). The organic layers were combined, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide 1.7 g of 2-(2-methoxyethyl)-7-(piperidin-4-yloxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-ylamine as a white solid.

Workup

  1. customAfter vigorous bubbling, a solution formed
  2. customevaporated (3×)
  3. dissolutionThe resulting oil was dissolved in brine (15 mL)
  4. extractionThe aqueous layer was extracted with dichloromethane (3×)
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-58418ccaedac4b02b241c8165b7b49c9
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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