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4-Toluenesulfonyl chloride → tert-butyl 2-[(4-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate

HRID 2203493
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HRID 2203493 반응식
[OH-].[NH4+:2].[CH2:3]([O:5][CH2:6][C:7]1[N:8]([CH2:32][CH2:33][CH3:34])[C:9]2[C:18]3[CH:17]=[C:16]([O:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:15]=[CH:14][C:13]=3[N+:12]([O-])=[CH:11][C:10]=2[N:31]=1)[CH3:4].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[C:25]([O:24][C:23](=[O:29])[NH:22][CH2:21][CH2:20][O:19][C:16]1[CH:15]=[CH:14][C:13]2[N:12]=[C:11]([NH2:2])[C:10]3[N:31]=[C:7]([CH2:6][O:5][CH2:3][CH3:4])[N:8]([CH2:32][CH2:33][CH3:34])[C:9]=3[C:18]=2[CH:17]=1)([CH3:28])([CH3:27])[CH3:26]
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참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 68973926tert-butyl 2-[(2-ethoxymethyl-5-oxido-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate

생성물 1

HCID 68974513tert-butyl 2-[(4-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate

시약·촉매·용매 1

HCID 6344Dichloromethane
용매
2회

실험 절차

Ammonium hydroxide (50 mL) was added to a solution of tert-butyl 2-[(2-ethoxymethyl-5-oxido-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate (9.7 g, 22 mmol) in dichloromethane (120 mL), and the mixture was cooled to 10° C. p-Toluenesulfonyl chloride (4.16 g, 21.8 mmol) was added in small portions, while maintaining the reaction temperature below 15° C. The reaction was stirred for 16 hours; a tan precipitate formed. Dichloromethane (500 mL) was added, and the precipitate was isolated by filtration and washed with diethyl ether to provide 3.98 g of tert-butyl[2-(4-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yloxy)ethyl]carbamate as a fine powder. The organic layer was washed sequentially with ammonium hydroxide, water, and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was recrystallized from acetonitrile to provide 4.4 g of tert-butyl 2-[(4-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate as a peach-colored powder.

후처리

  1. additionwas added in small portions
  2. temperaturewhile maintaining the reaction temperature below 15° C
  3. customa tan precipitate formed
  4. customthe precipitate was isolated by filtration
  5. washwashed with diethyl ether

출처 및 근거

ORD 기록
ord-c40168ffce154ad6aa2461a560daf26f
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365567B2

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