Triethylamine → HCID 11685281, compound

HRID 1714900Notes

Reaction equation

HRID 1714900 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][CH2:22][O:23][CH3:24].C(N(CC)CC)C.[C:32](Cl)(=[O:46])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]>ClCCl>[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:46])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[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 8471TriethylamineHCID 66986Myristoyl chlorideHCID 121062041-[2-(2-Aminoethoxy)ethyl]-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 11685281HCID 11685281, compoundYield 1.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, a mixture of 1-[2-(2-aminoethoxy)ethyl]-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine (444.5 mg, 1.349 mmol) in a mixture of dichloromethane (20.0 mL) and triethylamine (470 μL, 3.37 mmol) was cooled to 0° C. Myristoyl chloride (367 μL, 1.35 mmol) was slowly added over a period of 10 minutes. The reaction mixture was allowed to stir at 0° C. for 1 hour at which time analysis by thin layer chromatography indicated that there was no starting material left. The reaction mixture was diluted with dichloromethane (50 mL), washed with saturated sodium bicarbonate solution (2×15 mL), dried over magnesium sulfate and then concentrated under reduced pressure. The crude product was purified by column chromatography (20 g of silica gel eluted with 2% methanol in dichloromethane) followed by recrystallization from ethyl acetate (1.2 mL) and then further purified by column chromatography (25 g of silica gel eluted sequentially with 300 mL of 1% CMA in chloroform, 500 mL of 2% CMA in chloroform, 500 mL of 3% CMA in chloroform, 500 mL of 4% CMA in chloroform, 750 mL of 5% CMA in chloroform, and 600 mL of 6% CMA in chloroform) to provide 9.5 mg of N-(2-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)tetradecanamide as a white waxy solid, m.p. 85-87° C.

Workup

  1. waitleft
  2. washwashed with saturated sodium bicarbonate solution (2×15 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (20 g of silica gel eluted with 2% methanol in dichloromethane)
  6. customfollowed by recrystallization from ethyl acetate (1.2 mL)
  7. customfurther purified by column chromatography (25 g of silica gel
  8. washeluted sequentially with 300 mL of 1% CMA in chloroform

Sources & evidence

ORD record
ord-43dc6323a9e14b30a32528b91854fcaa
Source dataset
uspto-grants-2010_09
Patent number
US07799800B2

Reaction notes

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