Sodium Hydroxide → HCID 11574628, compound

HRID 1373982Notes

Reaction equation

HRID 1373982 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:25][O:26][CH2:27][CH3:28])[N:14]([NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([NH:22][CH2:23][CH3:24])=[O:21])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[OH-].[Na+]>C(O)(C(F)(F)F)=O.C(Cl)(Cl)Cl.CO.O.[Pt](=O)=O>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:25][O:26][CH2:27][CH3:28])[N:14]([NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([NH:22][CH2:23][CH3:24])=[O:21])[C:10]=2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

8

Reactant 2

HCID 14798Sodium HydroxideHCID 11574556HCID 11574556, compound

Product 1

HCID 11574628HCID 11574628, compoundYield 56.4%

Reagents, catalysts & solvents 5

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1-(3-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]amino}propyl)-3-ethylurea (0.700 g, 1.82 mmol) in 20 mL of TFA was treated with platinum (IV) oxide (0.413 g, 1.82 mmol). The mixture was placed under an atmosphere of nitrogen (3.8×105 Pa) and shaken at ambient temperature. After 22 h, the reaction mixture was diluted with 50 mL of CHCl3 and 10 mL of MeOH and filtered through a pad of CELITE filter agent. The pad was rinsed with 20% MeOH in CHCl3 until the filtrate ran clear. The filtrate was concentrated under reduced pressure to yield a clear, colorless oil. The oil was suspended in 25 mL of H2O and treated with 50% NaOH until the pH of the liquid reached 13. A white solid precipitated. The solid was triturated in the basic solution for 15 min and then filtered to give a white solid. The solid was recrystallized from MeCN to yield 1-(3-{[4-amino-2-(ethoxymethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]amino}propyl)-3-ethylurea (0.400 g) as white crystals. mp 189–191° C.; 1H NMR (300 MHz, DMSO-d6) δ 6.31 (t, J=5.9 Hz, 1H), 5.83–5.79 (m, 3H), 5.74 (t, J=5.6 Hz, 1H), 4.61 (s, 2H), 3.55 (q, J=7.0 Hz, 2H), 3.11–2.94 (m, 8H), 2.66 (t, J=5.8 Hz, 2H), 1.83–1.67 (m, 4H), 1.59 (p, J=6.9 Hz, 2H), 1.14 (t, J=7.0 Hz, 3H), 0.97 (t, J=7.1 Hz, 3H); 13C NMR (75 MHz, DMSO-d6) δ 158.4, 149.9, 149.3, 147.0, 137.6, 122.7, 105.5, 65.7, 63.3, 51.7, 37.5, 34.4, 32.5, 28.9, 23.2, 23.0, 22.4, 16.0, 15.3; MS (APCI) m/z 390 (M+H)+; Anal. Calcd for C19H31N7O2: C, 58.59; H, 8.02; N, 25.17; Found: C, 58.35; H, 8.30; N, 25.31.

Workup

  1. filtrationfiltered through a pad of CELITE
  2. filtrationfilter agent
  3. washThe pad was rinsed with 20% MeOH in CHCl3 until the filtrate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto yield a clear, colorless oil
  6. customA white solid precipitated
  7. customThe solid was triturated in the basic solution for 15 min
  8. filtrationfiltered
  9. customto give a white solid
  10. customThe solid was recrystallized from MeCN

Sources & evidence

ORD record
ord-444bdc3062f44e588c6033d153a48119
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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