Isopropanol → HCID 11647223, compound

HRID 1373965Notes

Reaction equation

HRID 1373965 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH: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][O:21][CH2:22][CH3:23].C(N(CC)CC)C.[CH:31]1([C:36](Cl)=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32]1.CC(O)C>C(Cl)Cl.O>[NH2:19][C:10]1[C:9]2[N:8]=[C:7]([CH2:20][O:21][CH2:22][CH3:23])[N:6]([NH:5][CH2:4][CH2:3][CH2:2][NH:1][C:36]([CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:37])[C:18]=2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:11]=1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 8471TriethylamineHCID 78284Cyclopentanecarbonyl chlorideHCID 86594228HCID 86594228, compound

Product 1

HCID 11647223HCID 11647223, compoundYield 16.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N1-(3-aminopropyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.500 g, 1.59 mmol) in 20 mL of CH2Cl2 was placed under an atmosphere of nitrogen, treated with triethylamine (0.443 mL, 3.34 mmol) and then cooled to 0° C. with an ice water bath. The reaction mixture was treated with cyclopentanecarbonyl chloride (0.203 mL, 1.67 mmol) over 2 min. The reaction was stirred and allowed to come to ambient temperature over 2 h. After 18 h, the reaction was quenched with 15 mL of 10% Na2CO3 solution. The mixture was diluted with 25 mL CHCl3, mixed and then separated. The organic portion was washed with H2O (15 mL) and brine (15 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield a tan foam. The foam was purified by chromatography (SiO2, 96:4 CHCl3: methanol (MeOH)) to yield a light tan solid. The solid was dissolved in boiling 2-propanol (IPA), cooled to ambient temperature and then water was added until an off-white solid precipitated from solution. The precipitate was triturated in the IPA/H2O mixture for 2 h and then collected by vacuum filtration to give N-(3-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]amino}propyl)cyclopentanecarboxamide (0.106 g) as an off-white solid. mp 75–77° C.;

Workup

  1. waitAfter 18 h
  2. customthe reaction was quenched with 15 mL of 10% Na2CO3 solution
  3. additionThe mixture was diluted with 25 mL CHCl3
  4. additionmixed
  5. customseparated
  6. washThe organic portion was washed with H2O (15 mL) and brine (15 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto yield a tan foam
  11. customThe foam was purified by chromatography (SiO2, 96:4 CHCl3: methanol (MeOH))
  12. customto yield a light tan solid
  13. dissolutionThe solid was dissolved
  14. temperaturecooled to ambient temperature
  15. customprecipitated from solution
  16. customThe precipitate was triturated in the IPA/H2O mixture for 2 h
  17. filtrationcollected by vacuum filtration

Sources & evidence

ORD record
ord-b87af3583c3244aeb32253e316dff2e2
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

Loading…