Water → N-[2-(2-amino-4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide hydrobromide

HRID 1097556ノート

反応式

HRID 1097556 の反応式
[N:1]#[C:2][Br:3].[NH2:4][C:5]1[C:6]([Cl:25])=[N:7][C:8]2[C:13]([C:14]=1[NH:15][CH2:16][C:17]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])([CH3:19])[CH3:18])=[CH:12][CH:11]=[CH:10][CH:9]=2.O>C(O)C>[BrH:3].[NH2:1][C:2]1[N:15]([CH2:16][C:17]([NH:20][S:21]([CH3:24])(=[O:22])=[O:23])([CH3:19])[CH3:18])[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([Cl:25])[C:5]=2[N:4]=1

参加物

5

反応物 3

HCID 962WaterHCID 10476Cyanogen BromideHCID 86626279HCID 86626279、化合物

生成物 1

HCID 86626280N-[2-(2-amino-4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide hydrobromide収率 15.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Cyanogen bromide (0.945 g, 8.93 mmol) was added to a solution of N-{2-[(3-amino-2-chloroquinolin-4-yl)amino]-1,1-dimethylethyl}methanesulfonamide (2.55 g, 7.44 mmol) in ethanol (25 mL), and the solution was stirred at ambient temperature for two hours. An analysis by HPLC indicated that no reaction had taken place, and the reaction was then heated overnight at 90° C. and allowed to cool to ambient temperature. Water was added; a precipitate was present and was isolated by filtration and washed with diethyl ether to provide 510 mg of N-[2-(2-amino-4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide hydrobromide as a brown solid. The filtrate was concentrated under reduced pressure, and the residue was dissolved in methanol. Diethyl ether was added, and a gummy precipitate formed, which was dissolved again in methanol and concentrated under reduced pressure to provide an additional 1.1 g of the product as a dark brown solid.

後処理

  1. temperaturethe reaction was then heated overnight at 90° C.
  2. temperatureto cool to ambient temperature
  3. customwas isolated by filtration
  4. washwashed with diethyl ether

出典と根拠

ORDレコード
ord-d7f8ac93c90d40b2b089f86cff394aa0
出典データセット
uspto-grants-2012_03
特許番号
US08143270B2

反応ノート

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