Triethylamine → HCID 22344435, compound

HRID 1839062Notes

Reaction equation

HRID 1839062 reaction equation
C(N(CC)CC)C.[CH2:8]([C:12]1[N:13]([CH2:25][CH2:26][CH2:27][NH2:28])[C:14]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:24]=1)[CH2:9][CH2:10][CH3:11].[CH3:29][S:30](Cl)(=[O:32])=[O:31]>ClCCl>[CH2:8]([C:12]1[N:13]([CH2:25][CH2:26][CH2:27][NH:28][S:30]([CH3:29])(=[O:32])=[O:31])[C:14]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:24]=1)[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 223444213-(2-Butyl-1H-imidazo[4,5-c]quinolin-1-yl)propan-1-amine

Product 1

HCID 22344435HCID 22344435, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.1 g, 10.6 mmol) was added with stirring to a solution of 3-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propylamine (2.00 g, 7.08 mmol) in dichloromethane (˜150 mL). Methanesulfonyl chloride (892 mg, 7.79 mmol) was added and the reaction was stirred under nitrogen overnight. The reaction mixture was washed with aqueous 1% sodium bicarbonate solution (3×50 mL). The aqueous washes were extracted with dichloromethane (2×20 mL). The organics were combined, dried over magnesium sulfate and then concentrated under reduced pressure to provide 1.89 g of N-[3-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]methanesulfonamide as a light brown solid.

Workup

  1. washThe reaction mixture was washed with aqueous 1% sodium bicarbonate solution (3×50 mL)
  2. extractionThe aqueous washes were extracted with dichloromethane (2×20 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-405451ba5a8248e691727aca580efbf8
Source dataset
uspto-grants-2004_01
Patent number
US06677349B1

Reaction notes

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