Triethylamine → HCID 86626278, compound

HRID 1097554

Reaction equation

HRID 1097554 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([NH:22][CH2:23][C:24]([CH3:27])([NH2:26])[CH3:25])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl>[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([NH:22][CH2:23][C:24]([NH:26][S:29]([CH3:28])(=[O:31])=[O:30])([CH3:27])[CH3:25])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride3×HCID 86227765N1-(2-chloro-3-nitroquinolin-4-yl)-2-methylpropane-1,2-diamine

Product 1

HCID 86626278HCID 86626278, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Triethylamine (1.77 mL, 12.7 mmol) was added to a solution of N1-(2-chloro-3-nitroquinolin-4-yl)-2-methylpropane-1,2-diamine (2.5 g, 8.5 mmol) in dichloromethane (25 mL), and the resulting solution was cooled to 0° C. and stirred for five minutes. Methanesulfonyl chloride (1.07 g, 9.33 mmol) was added in portions over a period of five minutes, and the reaction was allowed to warm to ambient temperature and stirred overnight. An analysis by high-performance liquid chromatography (HPLC) indicated the reaction was incomplete, and additional methanesulfonyl chloride (0.5 equivalent) was added. The reaction was stirred for two hours and again determined to be incomplete. Additional methanesulfonyl chloride (0.5 equivalent) and triethylamine (1.5 equivalents) were added, and the reaction was stirred for two hours and then diluted with dichloromethane. The resulting solution was washed twice with brine and twice with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 3.1 g of N-{2-[(2-chloro-3-nitroquinolin-4-yl)amino]-1,1-dimethylethyl}methanesulfonamide as a yellow solid.

Workup

  1. temperatureto warm to ambient temperature
  2. stirringstirred overnight
  3. stirringThe reaction was stirred for two hours
  4. stirringthe reaction was stirred for two hours
  5. washThe resulting solution was washed twice with brine and twice with saturated aqueous sodium bicarbonate
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4b5a29c76894433f8746c223dacfa0c9
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Linked notes

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