Triethylamine → HCID 23512676, compound

HRID 746581Notes

Reaction equation

HRID 746581 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][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][CH3:21].C(N(CC)CC)C.[CH:29]1([C:34](Cl)=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30]1>C(Cl)(Cl)Cl>[NH2:19][C:10]1[C:9]2[N:8]=[C:7]([CH2:20][CH3:21])[N:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:34]([CH:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[O:35])[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 8471TriethylamineHCID 78284Cyclopentanecarbonyl chlorideHCID 22344443HCID 22344443, compound

Product 1

HCID 23512676HCID 23512676, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1-(4-aminobutyl)-2-ethyl-1H-imidazo[4,5-c]quinolin-4-amine (1.00 g, 3.5 mmol) and triethylamine (0.64 mL, 4.6 mmol) in chloroform (100 mL) was cooled with an acetone/ice bath. Cyclopentanecarbonyl chloride (0.47 mL, 3.9 mmol) was slowly added. The reaction was complete within 10 minutes. The reaction mixture was washed with water (1×100 mL) and brine (1×100 mL). The organic layer was dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was slurried with acetonitrile. The resulting solid was isolated by filtration and dried in an oven overnight to provide 1.01 g of N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]cyclopentanecarboxamide as a light brown solid, m.p. 178.6-179.5° C. Analysis: Calculated for C22H29N5O-0.25H2O: % C, 68.81; % H, 7.74; % N, 18.24; Found: % C, 68.77; % H, 7.87; % N, 18.19.

Workup

  1. washThe reaction mixture was washed with water (1×100 mL) and brine (1×100 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting solid was isolated by filtration
  6. customdried in an oven overnight

Sources & evidence

ORD record
ord-7a9daf93d00545ef82d5a4a2d1d5a6da
Source dataset
uspto-grants-2008_07
Patent number
US07393859B2

Reaction notes

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