Benzoyl chloride → HCID 11741051, compound

HRID 432752Notes

Reaction equation

HRID 432752 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[CH3:21].C(N(CC)CC)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN1CCCC1=O>[NH2:20][C:11]1[C:10]2[N:9]=[C:8]([CH3:21])[N:7]([CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][C:29](=[O:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:19]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 10401692HCID 10401692, compound

Product 1

HCID 11741051HCID 11741051, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of the compound of Example 67, 1-[2-(2-aminoethoxy)ethyl]-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (1.47 g, 5.14 mmol) in 40 mL 1-methyl-2-pyrrolidinone was treated with triethylamine (1.43 mL, 10.3 mmol). With vigorous stirring, the solution was treated dropwise with benzoyl chloride (0.597 mL, 5.14 mmol). After 18 h, the reaction was concentrated. Purification by column chromatography (SiO2, 95:5:0.5 CHCl3:MeOH:NH4OH) gave a clear, colorless oil. The oil was triturated in ether and filtered to yield 531 mg of N-{2-[2-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethyl}benzamide as a white solid. mp 210-212° C.; 1H NMR (300 MHz, DMSO-d6) δ8.37 (t, J=7.0 Hz, 1 H), 8.05 (d, J=7.6 Hz, 1 H), 7.78-7.75 (m, 2 H), 7.61 (dd, J=1.1, 8.3 Hz, 1 H), 7.54-7.37 (m, 4 H), 7.21-7.16 (m, 1 H), 6.55 (s,2 H), 4.70 (t, J=5.0 Hz, 2 H), 3.90 (t, J=5.0 Hz, 2 H), 3.49 (t, J=6.1 Hz, 2 H), 3.34 (t, J=5.7 Hz, 2 H), 2.59 (s, 3 H); 13C NMR (75 MHz, DMSO-d6) δ166.7, 152.0, 151.1, 145.1, 134.8, 132.8, 131.4, 128.6, 127.4, 126.6, 121.3, 120.4,115.1, 69.4, 69.3, 45.8, 14.1; MS m/z 390 (M+H)+; Anal. Calcd for C22H23N5O2: C, 67.85; H, 5.95; N, 17.98. Found: C, 67.56; H, 5.81; N, 17.87.

Workup

  1. concentrationthe reaction was concentrated
  2. customPurification by column chromatography (SiO2, 95:5:0.5 CHCl3:MeOH:NH4OH)
  3. customgave a clear, colorless oil
  4. customThe oil was triturated in ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-bc4cf72bbaca4250ac15eb805d5d30af
Source dataset
uspto-grants-2003_12
Patent number
US06664265B2

Reaction notes

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