1,2-Diaminocyclohexane, trans- → HCID 69077219, compound

HRID 244863

Reaction equation

HRID 244863 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:5]=3[C:4]=2[CH:3]=1.[C:24]([NH2:29])(=[O:28])[CH:25]([CH3:27])[CH3:26].P([O-])([O-])([O-])=O.[K+].[K+].[K+].N[C@@H]1CCCC[C@H]1N>[Cu]I.O1CCOCC1>[CH2:22]([O:21][CH2:20][C:13]1[N:14]([CH2:15][C:16]([OH:18])([CH3:19])[CH3:17])[C:5]2[C:4]3[CH:3]=[C:2]([NH:29][C:24](=[O:28])[CH:25]([CH3:27])[CH3:26])[CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:12]=1)[CH3:23]

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 68424IsobutyramideHCID 69081224HCID 69081224, compound

Product 1

HCID 69077219HCID 69077219, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

1-[8-Bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol (0.550 g, 1.45 mmol), isobutyramide (0.150 g, 1.74 mmol), copper(I) iodide (0.055 g, 0.290 mmol), potassium phosphate (0.647 g, 3.05 mmol), and 1,4-dioxane (1.5 mL) were added to a scintillation vial. 1,2-(±)-trans-Diaminocyclohexane (0.035 mL, 0.290 mmol) was added. The vial was flushed with nitrogen, sealed with a Teflon-lined cap and heated at 110° C. for 72 hours. The vial was cooled to ambient temperature and the reaction was diluted with dichloromethane and methanol. Purification by chromatography with a HORIZON HPFC system (silica cartridge, eluting with a linear gradient of 1-15% CMA in chloroform) provided 0.38 g of N-[2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-8-yl]-2-methylpropanamide as a dark semi-solid.

Workup

  1. customThe vial was flushed with nitrogen
  2. customsealed with a Teflon-
  3. customlined cap
  4. temperatureThe vial was cooled to ambient temperature
  5. additionthe reaction was diluted with dichloromethane and methanol
  6. customPurification by chromatography with a HORIZON HPFC system (silica cartridge
  7. washeluting with a linear gradient of 1-15% CMA in chloroform)

Sources & evidence

ORD record
ord-53653b45511246d5a10afbdee9741c2d
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Linked notes

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