Triethylamine → HCID 21984427, compound

HRID 1818255Notes

Reaction equation

HRID 1818255 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:23]2[C:22]3[CH:21]=[CH:20][C:19]([Br:24])=[CH:18][C:17]=3[N:16]=[C:15]([NH2:25])[C:14]=2[N:13]=[C:12]1[CH2:26][O:27][CH2:28][CH3:29].C(N(CC)CC)C.[OH-].[Na+]>C(Cl)(Cl)Cl.O>[NH2:25][C:15]1[C:14]2[N:13]=[C:12]([CH2:26][O:27][CH2:28][CH3:29])[N:11]([CH2:10][CH2:9][CH2:8][CH2:7][NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[C:23]=2[C:22]2[CH:21]=[CH:20][C:19]([Br:24])=[CH:18][C:17]=2[N:16]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 219841661-(4-aminobutyl)-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 21984427HCID 21984427, compoundYield 120.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Methanesulfonyl chloride (0.44 mL, 5.7 mmol) was added to a suspension of 1-(4-aminobutyl)-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (2.04 g, 5.2 mmol) and triethylamine (0.94 mL, 6.8 mmol) in chloroform (100 mL), and the reaction was stirred for four hours. Water was added; a precipitate formed. The aqueous layer was adjusted to pH 10 with the addition of 50% aqueous sodium hydroxide. The precipitate was isolated by filtration, washed with cold chloroform, and dried overnight on the filter funnel. Material from another run was added, and entire procedure was repeated to eliminate unreacted starting material. N-{4-[4-Amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]butyl}methanesulfonamide (2.95 g) was obtained as a white solid.

Workup

  1. customa precipitate formed
  2. customThe precipitate was isolated by filtration
  3. washwashed with cold chloroform
  4. customdried overnight on the filter funnel
  5. additionMaterial from another run was added

Sources & evidence

ORD record
ord-01820f2ec6224537b97f76d8a87f881a
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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