HCID 21936597, compound → HCID 10108776, compound

HRID 432748Notes

Reaction equation

HRID 432748 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:28][CH3:29])[N:14]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][NH:20]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.CCO>[NH2:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][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[CH2:28][CH3:29]

Participants

4

Reactant 1

HCID 21936597HCID 21936597, compound

Product 1

HCID 10108776HCID 10108776, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Tert-butyl 2-[2-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate (9.35 g, 23.4 mmol) was suspended in 150 mL of 2M HCl in EtOH and the mixture was heated to reflux with stirring. After 2 h, the reaction was cooled to room temperature and the HCl salt of the product was collected by vacuum filtration and rinsed with ether. The free base was made by dissolving the HCl salt in water and treating with 10% NaOH solution until the mixture was pH 12. The aqueous suspension was extracted with CH2Cl2 (10×50 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give 6.62 g of 1-[2-(2-aminoethoxy)ethyl]-2-ethyl-1H-imidazo[4,5-c]quinolin-4-amine as a light yellow solid. mp=144-146° C.; 1H NMR (300 MHz, DMSO-d6) δ8.07 (d, J=7.5 Hz, 1 H), 7.61 (dd, J=1.0, 8.3 Hz, 1 H), 7.43-7.38 (m, 1 H), 7.25-7.17 (m, 1 H), 6.45 (s, 2 H), 4.71 (t, J=5.2 Hz, 2 H), 3.84 (t, J=5.2 Hz, 2 H), 3.27 (t, J=5.7 Hz, 2 H), 2.97 (q, J=7.5 Hz, 2 H), 2.51 (t, J=5.8 Hz, 2 H), 1.37 (t, J=7.5 Hz, 3 H), 1.25 (bs, 2 H); 13C NMR (75 MHz, DMSO-d6) δ155.2, 152.1, 145.1, 132.8, 126.6, 126.6, 121.3, 120.5, 115.2, 73.8, 69.4, 45.4, 41.6, 20.4, 12.2; MS m/z 300 (M+H)+; Anal. Calcd for C16H21N5O: C, 64.19; H, 7.07; N, 23.39. Found: C, 63.98; H, 6.96; N, 23.27.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. filtrationthe HCl salt of the product was collected by vacuum filtration
  4. washrinsed with ether
  5. dissolutionby dissolving the HCl salt in water
  6. additiontreating with 10% NaOH solution until the mixture
  7. extractionThe aqueous suspension was extracted with CH2Cl2 (10×50 mL)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f22326eca9d348f5a5b733b84f4bbad1
Source dataset
uspto-grants-2003_12
Patent number
US06664265B2

Reaction notes

Loading…