Phenyl isocyanate → N-(2-{2-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy)ethyl)-N'-phenylurea

HRID 1793136Notes

Reaction equation

HRID 1793136 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[C:8]1[CH2:21][CH2:22][O:23][CH3:24].[C:25]1([N:31]=[C:32]=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CCN(CC)CC>C(Cl)Cl>[NH2:20][C:11]1[C:10]2[N:9]=[C:8]([CH2:21][CH2:22][O:23][CH3:24])[N:7]([CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][C:32]([NH:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:33])[C:19]=2[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[N:12]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 120960451-[2-(2-aminoethoxy)ethyl]-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 10204394N-(2-{2-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy)ethyl)-N'-phenylureaYield 36.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-[2-(2-Aminoethoxy)ethyl]-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine (919 mg, 2.76 mmol) was dissolved in 30 mL of anhydrous CH2Cl2 and cooled to 0° C. under N2. The reaction mixture was then treated with phenyl isocyanate (300 μL, 2.76 mmol) and Et3N (0.77 mL, 5.51 mmol) and allowed to warm slowly to room temperature. After stirring overnight, the reaction mixture was then quenched by addition of saturated NaHCO3 solution (30 mL). The organic layer was separated and washed with H2O and brine, dried over Na2SO4 and concentrated under reduced pressure to give a yellow solid. The solid was triturated with Et2O (30 mL) and a few drops of MeOH. The solid was isolated by filtration and dried under vacuum to give 460 mg of N-(2-{2-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)-N′-phenylurea as a white powder. m.p. 180-182° C.; MS 453 (M+H)+;1H NMR (300 MHz, DMSO-d6) δ 8.51 (s, 1H); 7.37 (d, J=7.7 Hz, 2H); 7.19 (t, J=8.2 Hz, 2H); 6.86 (t, J=7.7 Hz, 1H); 6.11 (t, J=5.5 Hz, 2H); 5.70 (s, 2H); 4.43 (t, J=5.1 Hz, 2H); 3.78-3.69 (m, 4H); 3.39 (t, J=5.6 Hz, 2H); 3.25 (s, 3H); 3.19 (m, 2H); 3.10 (t, J=6.8 Hz, 2H); 2.91 (m, 2H); 2.64 (m, 2H); 1.72 (m, 4H); 13C (75 MHz, DMSO-d6) δ 155.5, 151.3, 149.3, 146.3, 140.8, 138.5, 129.0, 125.0, 121.4, 118.0, 105.6, 70.6, 70.5, 70.4, 58.4, 44.6, 39.2, 32.7, 27.6, 23.8, 23.1, 23.0; Anal. Calcd for C24H32N6O3: % C, 63.70, % H, 7.13, % N, 18.57. Found: % C, 63.33, % H, 7.16, % N, 18.66.

Workup

  1. temperatureto warm slowly to room temperature
  2. customthe reaction mixture was then quenched by addition of saturated NaHCO3 solution (30 mL)
  3. customThe organic layer was separated
  4. washwashed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto give a yellow solid
  8. customThe solid was triturated with Et2O (30 mL) and a few drops of MeOH
  9. customThe solid was isolated by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-dad8df40988e4f31b87f0a164dd34f68
Source dataset
uspto-grants-2006_07
Patent number
US07078523B2

Reaction notes

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