4-Toluenesulfonyl chloride → N-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-8-yl]-2-methylpropanamide

HRID 244864

반응식

HRID 244864 반응식
ClC1C=C(C=CC=1)C(OO)=O.[CH2:12]([O:14][CH2:15][C:16]1[N:17]([CH2:35][C:36]([OH:39])([CH3:38])[CH3:37])[C:18]2[C:27]3[CH:26]=[C:25]([NH:28][C:29](=[O:33])[CH:30]([CH3:32])[CH3:31])[CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][C:19]=2[N:34]=1)[CH3:13].[OH-].[NH4+:41].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[NH2:41][C:20]1[C:19]2[N:34]=[C:16]([CH2:15][O:14][CH2:12][CH3:13])[N:17]([CH2:35][C:36]([OH:39])([CH3:37])[CH3:38])[C:18]=2[C:27]2[CH:26]=[C:25]([NH:28][C:29](=[O:33])[CH:30]([CH3:31])[CH3:32])[CH:24]=[CH:23][C:22]=2[N:21]=1

참가 물질

6

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69077219N-[2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-8-yl]-2-methylpropanamide

생성물 1

HCID 57657238N-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-8-yl]-2-methylpropanamide

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

3-Chloroperoxybenzoic acid (60% pure, 0.283 g, 1.0 mmol) was added to a solution of N-[2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-8-yl]-2-methylpropanamide (0.380 g, 1.0 mmol) in chloroform (10 mL) and the reaction was stirred for 1 hour. The mixture was cooled in an ice bath and ammonium hydroxide (3 mL) was added. After 15 minutes of stirring, p-toluenesulfonyl chloride (0.190 g, 1.0 mmol) was added and the reaction mixture was stirred for 72 hours. The fractions were separated and the aqueous fraction was extracted with chloroform. The combined organic fractions were washed with brine and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a linear gradient of 2-20% CMA in chloroform). Recrystallization from acetonitrile provided 0.231 g of N-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-8-yl]-2-methylpropanamide as an off-white solid, mp 259-261° C.

후처리

  1. temperatureThe mixture was cooled in an ice bath
  2. stirringAfter 15 minutes of stirring
  3. stirringthe reaction mixture was stirred for 72 hours
  4. customThe fractions were separated
  5. extractionthe aqueous fraction was extracted with chloroform
  6. washThe combined organic fractions were washed with brine
  7. custompurified by chromatography
  8. washeluting with a linear gradient of 2-20% CMA in chloroform)
  9. customRecrystallization from acetonitrile

출처 및 근거

ORD 기록
ord-f8a6b5cbb6b64915903855bdcfe78e0e
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658666B2

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