Hydrochloric Acid → HCID 86594228, compound

HRID 1373934Notes

Reaction equation

HRID 1373934 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:27][O:28][CH2:29][CH3:30])[N:14]([NH:15][CH2:16][CH2:17][CH2:18][NH:19]C(=O)OC(C)(C)C)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.Cl.[OH-].[Na+]>C(O)C.O>[NH2:19][CH2:18][CH2:17][CH2:16][NH:15][N:14]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=[C:13]1[CH2:27][O:28][CH2:29][CH3:30]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86596851HCID 86596851, compound

Product 1

HCID 86594228HCID 86594228, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of tert-butyl {3-[(4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)amino]propyl}carbamate (1.30 g, 3.14 mmol) in 10 mL of ethanol was treated with a solution of 3 M hydrogen chloride in ethanol (5.0 mL, 15 mmol) and heated to 100° C. After 30 min, the solvent was concentrated under reduced pressure to yield a brown sludge. The material was triturated with diethyl ether and filtered to give a tan solid. The solid was dissolved in water and treated with 10% NaOH solution until pH 13 was reached. The aqueous solution was extracted with CH2Cl2 (4×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield N1-(3-aminopropyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.77 g) as a gold colored foam.

Workup

  1. concentrationthe solvent was concentrated under reduced pressure
  2. customto yield a brown sludge
  3. customThe material was triturated with diethyl ether
  4. filtrationfiltered
  5. customto give a tan solid
  6. extractionThe aqueous solution was extracted with CH2Cl2 (4×)
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c5a1b6f442b84653b6aa30594ab4b313
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

Loading…