Methanol → HCID 10477994, compound

HRID 1373936Notes

Reaction equation

HRID 1373936 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[C:10]([NH2:19])[C:9]=2[N:8]=[C:7]1[CH2:20][O:21][CH2:22][CH3:23].[C:24]1([N:30]=[C:31]=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(Cl)(Cl)Cl.CO>C(Cl)Cl>[NH2:19][C:10]1[C:9]2[N:8]=[C:7]([CH2:20][O:21][CH2:22][CH3:23])[N:6]([NH:5][CH2:4][CH2:3][CH2:2][NH:1][C:31]([NH:30][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:32])[C:18]=2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:11]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 7672Phenyl isocyanateHCID 86594228HCID 86594228, compound

Product 1

HCID 10477994HCID 10477994, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N1-(3-aminopropyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.250 g, 0.795 mmol) in 10 mL of CH2Cl2 was cooled to 0° C. under an atmosphere of nitrogen. The reaction mixture was treated dropwise with phenyl isocyanate (0.091 mL, 0.835 mmol). After 16 h, the reaction mixture was quenched by 10% Na2CO3 solution, diluted with CHCl3 and the phases were separated. The organic portion was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield an off-white solid. Chromatography (SiO2, 95:5 CHCl3:MeOH) gave an off-white foam. The foam was triturated with diethyl ether and filtered to give 1-{3-[(4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)amino]propyl}-3-phenylurea (0.115 g) as an off-white solid. mp 177–179° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.46 (dd, J=8.1, 1.0 Hz, 1H), 8.39 (s, 1H), 7.58 (dd, J=8.4, 0.9 Hz, 1H), 7.44–7.35 (m, 3H), 7.25–7.18 (m, 3H), 6.99 (t, J=5.6 Hz, 1H), 6.90–6.85 (m, 1H), 6.60 (s, 2H), 6.16 (t, J=5.6 Hz, 1H), 4.76 (s, 2H), 3.60 (q, J=7.0 Hz, 2H), 3.26–3.18 (m, 4H), 1.76 (t, J=7.0 Hz, 2H), 1.15 (t, J=7.0 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 155.2, 151.8, 149.0, 144.8, 140.4, 132.0, 128.5, 126.9, 125.7, 123.7, 120.9, 120.8, 120.8, 117.6, 114.3, 65.4, 62.7, 49.7, 37.0, 28.1, 14.9; MS (APCI) m/z 434 (M+H)+; Anal. Calcd for C23H27N7O2: C, 63.72; H, 6.28; N, 22.62; Found: C, 63.45; H, 6.04; N, 22.28.

Workup

  1. customthe reaction mixture was quenched by 10% Na2CO3 solution
  2. additiondiluted with CHCl3
  3. customthe phases were separated
  4. washThe organic portion was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto yield an off-white solid
  9. customThe foam was triturated with diethyl ether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-4c9fd170d90d4e8395237b7d5c4cd39a
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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