Triethylamine → HCID 67051137, compound

HRID 598376Notes

Reaction equation

HRID 598376 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[CH:14][C:13]3[N:19]=[C:20]([CH2:27][O:28][CH2:29][CH3:30])[N:21]([CH2:22][C:23]([NH2:26])([CH3:25])[CH3:24])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:38]1([C:44](Cl)=[O:45])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[CH:14][C:13]3[N:19]=[C:20]([CH2:27][O:28][CH2:29][CH3:30])[N:21]([CH2:22][C:23]([NH:26][C:44]([CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)=[O:45])([CH3:24])[CH3:25])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 67051107HCID 67051107, compound

Product 1

HCID 67051137HCID 67051137, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(8-Benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethylamine (2.19 g, 5.4 mmol), triethylamine (1.5 mL, 10.8 mmol), and dichloromethane (50 mL) were combined. Cyclohexanecarbonyl chloride (0.95 mL, 6.0 mmol) was added and the reaction was stirred overnight. Saturated sodium bicarbonate was added and the layers were separated. The organic fraction was sequentially washed with a second portion of saturated sodium bicarbonate and then brine; dried over sodium sulfate; filtered; and concentrated under reduced pressure to provide an orange foam. The residue was purified by column chromatography on a HORIZON HPFC system. A silica gel cartridge was used eluting with a gradient of 0-20% CMA in chloroform to provide 2.34 g of N-{2-[8-(benzyloxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}cyclohexanecarboxamide as a tan solid.

Workup

  1. customthe layers were separated
  2. washThe organic fraction was sequentially washed with a second portion of saturated sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationand concentrated under reduced pressure
  6. customto provide an orange foam
  7. customThe residue was purified by column chromatography on a HORIZON HPFC system
  8. washA silica gel cartridge was used eluting with a gradient of 0-20% CMA in chloroform

Sources & evidence

ORD record
ord-8f9dbbedac084db49cf50127b24aea71
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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