Water → HCID 21936600, compound

HRID 432754Notes

Reaction equation

HRID 432754 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[C:8]1[CH2:21][O:22][CH2:23][CH3:24].C(N(CC)CC)C.[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.O>C(Cl)Cl>[NH2:20][C:11]1[C:10]2[N:9]=[C:8]([CH2:21][O:22][CH2:23][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[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 10359216HCID 10359216, compound

Product 1

HCID 21936600HCID 21936600, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the compound of Example 69, 1-[2-(2-aminoethoxy)ethyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine (0.98 g, 2.98 mmol) in 20 mL CH2Cl2 was treated with triethylamine (1.04, 7.45 mmol) and chilled in an ice water bath. With vigorous stirring, the solution was treated dropwise with benzoyl chloride (0.363 mL, 3.13 mmol). After 18 h, the reaction was treated with 25 mL water and 25 mL CH2Cl2 and the layers were separated. The organic portion was washed with 1% Na2CO3 solution, water, brine, dried over Na2SO4, filtered and concentrated to yield a yellow foam. Purification by column chromatography (SiO2, 95:5:0.5 CHCl3:MeOH:NH4OH) followed by recrystallization from CH2Cl2/hexanes gave 422 mg of N-(2-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)benzamide as a light yellow powder. mp=154-156° C.; 1H NMR (300 MHz, DMSO-d6) δ8.36 (t, J=5.3 Hz, 1 H), 8.08 (d, J=8.0 Hz, 1 H), 7.82-7.73 (m, 2 H), 7.62 (d, J=8.3 Hz, 1 H), 7.55-7.40 (m, 4 H), 7.20 (t, J=8.2 Hz, 1 H), 6.58 (s, 2 H), 4.82 (t, J=5.3 Hz, 2 H), 4.75 (s, 2 H), 3.91 (t, J=5.2 Hz, 2 H), 3.54-3.45 (m, 4 H), 3.38 (q, J=5.2 Hz, 2 H), 1.13 (t, J=7.0 Hz, 3 H); 13C NMR (75 MHz, DMSO-d6) δ166.7, 152.3, 149.9, 145.6, 134.8, 133.5, 131.4, 128.6, 127.5, 127.1, 126.7, 121.4, 120.8, 115.1, 69.5, 69.2, 65.7, 64.7, 45.7, 15.3; MS m/z 434 (M+H)+; Anal. Calcd for C24H27N5O3: C, 66.50; H, 6.28; N, 16.15. Found: C, 66.24; H, 6.31; N, 15.96.

Workup

  1. temperaturechilled in an ice water bath
  2. customthe layers were separated
  3. washThe organic portion was washed with 1% Na2CO3 solution, water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a yellow foam
  8. customPurification by column chromatography (SiO2, 95:5:0.5 CHCl3:MeOH:NH4OH)
  9. customfollowed by recrystallization from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-e30b8506164f47f2b02087389c611736
Source dataset
uspto-grants-2003_12
Patent number
US06664265B2

Reaction notes

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