Water → HCID 11696190, compound

HRID 1373980Notes

Reaction equation

HRID 1373980 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:23][O:24][CH2:25][CH3:26])[N:14]([NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.O.[OH-].[Na+]>C(O)(C(F)(F)F)=O.C(Cl)(Cl)Cl.[Pt](=O)=O>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:23][O:24][CH2:25][CH3:26])[N:14]([NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21])[C:10]=2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

7

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 11710146HCID 11710146, compound

Product 1

HCID 11696190HCID 11696190, compoundYield 28.5%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-(3-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]amino}propyl)acetamide (0.220 g, 0.617 mmol) in 15 mL of TFA was treated with platinum (IV) oxide (0.140 g, 0.617 mmol). The mixture was placed under an atmosphere of hydrogen (3.8×105 Pa) and shaken at ambient temperature. After 18 h, the reaction mixture was diluted with CHCl3 (15 mL) and filtered through a pad of CELITE filter agent and rinsed with several portions of CHCl3 (1% TFA). The filtrate was concentrated under reduced pressure to yield an off-white oil. The oil was suspended in a minimum amount of H2O and treated with 50% NaOH solution until the pH of the liquid was 12–13. The mixture was extracted with CH2Cl2 (3×15 mL). The combined organic extracts were washed with brine (15 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield an off-white solid. The solid was purified by chromatography (SiO2, 15–20% (80:18:2 CHCl3:MeOH:NH4OH) in CHCl3) to yield a white solid. The solid was recrystallized from MeCN to yield N-(3-{[4-amino-2-(ethoxymethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]amino}propyl)acetamide (0.0633 g) as white crystals. mp 198–200° C.; 1H NMR (500 MHz, DMSO-d6) δ 7.80 (t, J=5.0 Hz, 1H), 6.30 (t, J=6.0 Hz, 1H), 5.78 (s, 2H), 4.61 s, 2H), 3.55 (q, J=7.0 Hz, 2H), 3.12 (q, J=6.7 Hz, 2H), 3.05–3.01 (m, 4H), 2.66 (t, J=5.9 Hz, 2H), 1.78–1.73 (m, 7H), 1.62 (p, J=7.1 Hz, 2H), 1.14 (t, J=7.0 Hz, 3H); 13C NMR (125 MHz DMSO-d6) δ 169.4, 149.9, 149.3, 147.1, 137.6, 122.7, 105.5, 65.7, 63.4, 51.6, 36.8, 32.5, 27.9, 23.9, 23.0, 23.0, 22.5, 15.3; MS (APCI) m/z 361 (M+H)+; Anal. Calcd for C18H28N6O2: C, 59.98; H, 7.83; N, 23.31;

Workup

  1. filtrationfiltered through a pad of CELITE
  2. filtrationfilter agent
  3. washrinsed with several portions of CHCl3 (1% TFA)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto yield an off-white oil
  6. extractionThe mixture was extracted with CH2Cl2 (3×15 mL)
  7. washThe combined organic extracts were washed with brine (15 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto yield an off-white solid
  12. customThe solid was purified by chromatography (SiO2, 15–20% (80:18:2 CHCl3:MeOH:NH4OH) in CHCl3)
  13. customto yield a white solid
  14. customThe solid was recrystallized from MeCN

Sources & evidence

ORD record
ord-51b2de1027e14df8bf359c9e8fce7726
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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