Hydrochloric Acid → HCID 69435139, compound

HRID 1373970Notes

Reaction equation

HRID 1373970 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:19][O:20][CH2:21][CH3:22])[N:14]([NH:15][CH:16]([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:23][CH2:24][CH2:25][CH2:26][NH:27]C(=O)OC(C)(C)C)=[CH:5][C:4]=2[N:3]=1.Cl.[OH-].[Na+]>C(O)C.O>[NH2:27][CH2:26][CH2:25][CH2:24][O:23][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[N:14]([NH:15][CH:16]([CH3:17])[CH3:18])[C:13]([CH2:19][O:20][CH2:21][CH3:22])=[N:12][C:11]=3[C:2]([NH2:1])=[N:3][C:4]=2[CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10050492HCID 10050492, compound

Product 1

HCID 69435139HCID 69435139, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of tert-butyl [3-(4-amino-2-ethoxymethyl-1-isopropylamino-1H-imidazo[4,5-c]quinolin-7-yloxy)propyl]carbamate (1.24 g, 2.62 mmol) in 5 mL of ethanol (EtOH) was treated with 5 mL of 4.3 M HCl in EtOH. The reaction was heated to 100° C. After 1 h, the reaction was cooled to ambient temperature and concentrated under reduced pressure to yield a brown solid. The solid was dissolved in a minimum amount of H2O and treated with 10% NaOH solution until the pH of the liquid was 13. The basic aqueous mixture was extracted with CH2Cl2 (3×25 mL). The combined organic extracts were washed with brine (25 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield 7-(3-aminopropoxy)-2-ethoxymethyl-N1-isopropyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.84 g) as a tan solid.

Workup

  1. temperaturethe reaction was cooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. customto yield a brown solid
  4. extractionThe basic aqueous mixture was extracted with CH2Cl2 (3×25 mL)
  5. washThe combined organic extracts were washed with brine (25 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-06a15473259e47258aebad859622e4f9
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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