Diethyl Ether → N-(2-{2-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)benzamide

HRID 432728Notes

Reaction equation

HRID 432728 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].CCN(CC)CC.[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CCOCC>C(Cl)Cl.CO>[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](=[O:39])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:19]=2[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[N:12]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7412Benzoyl chlorideHCID 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 21936602N-(2-{2-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)benzamideYield 36.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 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 (1.00 g, 3.00 mmol) was dissolved in 30 mL of anhydrous CH2Cl2 and cooled to 0° C. under N2. To the stirred solution were added Et3N (0.84 mL, 6.00 mmol) and benzoyl chloride (348 μL, 3.00 mmol) and the reaction was allowed to warm to room temperature 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 oil. The oil was dissolved in a minimum amount of hot MeOH and then treated with Et2O (50 mL) which caused a white percipitate to form. The solid was isolated by filtration and dried under vacuum to give 476 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)benzamide as a white powder. m.p. 141-143° C.; MS 438 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ8.36 (t, J=5.4 Hz, 1 H); 7.78-7.76 (m, 2 H); 7.54-7.42 (m, 3 H); 5.68 (s, 2 H); 4.43 (t, J=5.4 Hz, 2 H); 3.75-3.69 (m, 4 H); 3.48 (t, J=6.0 Hz, 2 H); 3.37 (t, J=5.5 Hz, 2 H); 3.24 (s, 3 H); 3.07 (t, J=6.9 Hz, 2 H); 2.91 (m, 2 H); 2.63 (m, 2 H); 1.70 (m, 4 H); 13C (75 MHz, DMSO-d6) δ166.7, 151.3, 149.3, 146.2, 138.5, 134.8, 131.4, 128.6, 127.5, 124.9, 105.6, 70.5, 70.5, 69.3, 58.4, 44.6, 32.7, 27.6, 23.8, 23.0, 23.0. Anal. Calcd for C24H31N5O3: %C, 65.88; %H, 7.14; %N, 16.01. Found: %C, 65.55; %H, 7.15; %N, 15.87.

Workup

  1. temperatureto warm to room temperature overnight
  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 oil
  8. customto form
  9. customThe solid was isolated by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-80a4b3b19c6c49e9a4769d329d6bfe0e
Source dataset
uspto-grants-2003_12
Patent number
US06664265B2

Reaction notes

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