Triethylamine → HCID 86611426, compound

HRID 2203547Notes

Reaction equation

HRID 2203547 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([OH:15])=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:16]=1)[CH3:2].C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C(Cl)(Cl)Cl>[CH3:33][S:34]([O:15][C:11]1[CH:12]=[CH:13][C:14]2[C:5]3[N:4]([CH2:17][CH2:18][O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:3]([CH2:1][CH3:2])=[N:16][C:6]=3[CH:7]=[N:8][C:9]=2[CH:10]=1)(=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 136347848HCID 136347848, compound

Product 1

HCID 86611426HCID 86611426, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Ethyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-7-ol (1.5 g, 4.5 mmol), chloroform (45 mL), and triethylamine (0.697 mL, 5.00 mmol) were combined. Methanesulfonyl chloride (0.348 mL, 4.50 mmol) was added dropwise to the mixture; a flocculent precipitate formed. The reaction was stirred for 72 hours and then quenched with methanol. The volatiles were removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluting with a dichloromethane:methanol gradient) to provide 0.628 g of 2-ethyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-7-yl methanesulfonate as a white solid.

Workup

  1. customa flocculent precipitate formed
  2. customquenched with methanol
  3. customThe volatiles were removed under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (
  5. washeluting with a dichloromethane

Sources & evidence

ORD record
ord-7baded6ab750413d90f49d40b7b227b8
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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