Water → HCID 10431280, compound

HRID 432753Notes

Reaction equation

HRID 432753 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][CH3:22].C(N(CC)CC)C.[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.O>C(Cl)Cl.C(Cl)(Cl)Cl>[NH2:20][C:11]1[C:10]2[N:9]=[C:8]([CH2:21][CH3:22])[N:7]([CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][C:30](=[O:37])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:19]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 10108776HCID 10108776, compound

Product 1

HCID 10431280HCID 10431280, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the compound of Example 68, 1-[2-(2-aminoethoxy)ethyl]-2-ethyl-1H-imidazo[4,5-c]quinolin-4-amine (800 mg, 2.67 mmol) in 30 mL of CH2Cl2 was treated with triethylamine (1.10 mL, 8.0 mmol). With vigorous stirring the solution was treated dropwise with benzoyl chloride (0.325 mL, 2.80 mmol). After 18 h, the reaction was treated with 50 mL water and 50 mL CHCl3 and the layers were separated. The aqueous portion was extracted with CHCl3 (3×30 mL). The combined organic portions were washed with brine, dried over Na2SO4, filtered and concentrated to yield an off white solid. Purification by column chromatography (SiO2, 95:5:0.5 CHCl3:MeOH:NH4OH) gave 574 mg of N-{2-[2-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethyl}benzamide as a white solid. mp=188-191° C.; 1H NMR (300 MHz, DMSO-d6) δ8.36 (t, J=5.4 Hz, 1 H), 8.04 (d, J=7.5 Hz, 1 H), 7.80-7.75 (m, 2 H), 7.62 (dd, J=1.1, 8.3 Hz, 1 H), 7.55-7.36 (m, 4 H), 7.18 (m, 1 H), 6.45 (s, 2 H), 4.70 (t, J=5.1 Hz, 2 H), 3.90 (t, J=5.1 Hz, 2 H), 3.49 (t, J=6.1 Hz, 2 H), 3.40-3.33 (m, 2 H), 2.93 (q, J=7.5 Hz, 2 H), 1.30 (t, J=7.4 Hz, 3 H); 13C NMR (75 MHz, DMSO-d6) δ166.7, 155.2, 152.0, 145.1, 134.8, 132.8, 131.4, 128.6, 127.5, 126.7, 126.6, 121.4, 120.5, 115.2, 69.4, 69.2, 45.4, 20.3, 12.1; MS m/z 404 (M+H)+; Anal. Calcd for C23H25N5O2: C, 68.47; H, 6.25; N, 17.36. Found: C, 68.27; H, 6.32; N, 17.28.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous portion was extracted with CHCl3 (3×30 mL)
  3. washThe combined organic portions were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield an off white solid
  8. customPurification by column chromatography (SiO2, 95:5:0.5 CHCl3:MeOH:NH4OH)

Sources & evidence

ORD record
ord-d037a504c14140d5be2b5a02795fed84
Source dataset
uspto-grants-2003_12
Patent number
US06664265B2

Reaction notes

Loading…