HCID 10108777, compound → HCID 10017869, compound

HRID 1373921Notes

Reaction equation

HRID 1373921 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH:19][CH:20]([CH3:22])[CH3:21])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)[CH3:2]>FC(F)(F)C(O)=O.[Pt](=O)=O>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH:19][CH:20]([CH3:21])[CH3:22])[C:7]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)[CH3:2]

Participants

4

Reactant 1

HCID 10108777HCID 10108777, compound

Product 1

HCID 10017869HCID 10017869, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-ethoxymethyl-N1-isopropyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.700 g, 2.34 mmol) in 25 mL of trifluroacetic acid was treated with platinum(IV) oxide (0.27 g, 1.2 mmol) and the mixture was shaken under an atmosphere of hydrogen (3.8×105 Pa). After 15 h, the reaction mixture was filtered through a pad of CELITE filter agent, rinsed with 9:1:0.5 CHCl3:MeOH:trifluoroacetic acid (TFA) and concentrated under reduced pressure to yield a creamy white solid. The solid was triturated with concentrated NH4OH solution for 2 h and then extracted with CHCl3 (3×). The organic portion was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield a white foam. The foam was triturated with diethyl ether, filtered and dried under reduced pressure to yield 2-ethoxymethyl-N1-isopropyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.376 g) as a fine white solid. mp 144–146° C.; 1H NMR (300 MHz, CDCl3) δ 5.08 (d, J=2.7 Hz, 1H), 4.92 (s, 2H), 4.78 (s, 2H), 3.61 (q, J=7.0 Hz, 2H), 3.53–3.43 (m, 1H), 3.07–3.03 (m, 2H), 2.85–2.81 (m, 2H), 1.92–1.79 (m, 4H), 1.25 (t, J=7.0 Hz, 3H), 1.08 (d, J=6.3 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ 149.4, 148.9, 148.1, 138.8, 122.9, 107.4, 66.6, 65.4, 53.0, 32.5, 23.7, 23.2, 22.8, 20.5, 15.1; MS (APCI) m/z 304 (M+H)+; Anal. Calcd for C16H25N5O: C, 63.34; H, 8.31; N, 23.08; Found: C, 63.32; H, 8.31; N, 22.97.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washrinsed with 9:1:0.5 CHCl3
  4. concentrationMeOH:trifluoroacetic acid (TFA) and concentrated under reduced pressure
  5. customto yield a creamy white solid
  6. customThe solid was triturated with concentrated NH4OH solution for 2 h
  7. extractionextracted with CHCl3 (3×)
  8. washThe organic portion was washed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customto yield a white foam
  13. customThe foam was triturated with diethyl ether
  14. filtrationfiltered
  15. customdried under reduced pressure

Sources & evidence

ORD record
ord-843b16144b5246ea81465c869966b49f
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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