Acetyl chloride → HCID 11710146, compound

HRID 1373975Notes

Reaction equation

HRID 1373975 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(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32]>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](=[O:33])[CH3:32])[C:18]=2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:11]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86594228HCID 86594228, compound

Product 1

HCID 11710146HCID 11710146, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N1-(3-aminopropyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (1.00 g, 3.18 mmol) in 15 mL of CH2Cl2 was placed under an atmosphere of nitrogen. The solution was chilled in an ice water bath and treated first with triethylamine (0.89 mL, 6.7 mmol) and then slowly with acetyl chloride (0.89 mL, 3.3 mmol). After 2 h, the reaction was warmed to ambient temperature, quenched with 15 mL of saturated NaHCO3 solution and diluted with 30 mL of CHCl3. The phases were separated and the organic portion was washed with H2O (15 mL) and brine (15 mL). The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure to yield a light yellow foam. The foam was crystallized from MeCN to give light yellow crystals. The crystals were pulverized and then triturated with Et2O for 18 h and filtered off to yield N-(3-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]amino}propyl)acetamide (0.728 g) as a white solid. mp 178–181° C.; 1H NMR (500 MHz, DMSO-d6) δ 8.44 (d, J=8.1 Hz, 1H), 7.82 (t, J=5.1 Hz, 1H), 7.59 (d, J=8.2 Hz, 1H), 7.45–7.42 (m, 1H), 7.26–7.22 (m, 1H), 6.96 (t, J=5.6 Hz, 1H), 6.59 (s, 2H), 4.75 (s, 2H), 3.61 (q, J=7.0 Hz, 2H), 3.20–3.14 (m, 4H), 1.77 (s, 3H), 1.71 (p, J=7.0 Hz, 2H), 1.17 (t, J=7.0Hz, 3H);

Workup

  1. temperatureThe solution was chilled in an ice water bath
  2. customquenched with 15 mL of saturated NaHCO3 solution
  3. additiondiluted with 30 mL of CHCl3
  4. customThe phases were separated
  5. washthe organic portion was washed with H2O (15 mL) and brine (15 mL)
  6. dry with materialThe organic portion was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto yield a light yellow foam
  10. customThe foam was crystallized from MeCN
  11. customto give light yellow crystals
  12. customtriturated with Et2O for 18 h
  13. filtrationfiltered off

Sources & evidence

ORD record
ord-84c25015cc0d4fdd92bc4291764dad30
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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