4-Toluenesulfonyl chloride → HCID 67262961, 화합물

HRID 1925474노트

반응식

HRID 1925474 반응식
ClC1C=C(C=CC=1)C(OO)=O.[Cl:12][CH2:13][C:14]1[N:15]([CH2:27][CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[C:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[CH:18][C:17]=2[N:26]=1.[OH-].[NH4+:35].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl.O>[Cl:12][CH2:13][C:14]1[N:15]([CH2:27][CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[C:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[C:18]([NH2:35])[C:17]=2[N:26]=1

참가 물질

7

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 672629742-(chloromethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline

생성물 1

HCID 67262961HCID 67262961, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

3-Chloroperoxybenzoic acid (mCPBA) (3.8 g of 77% pure material, 14.2 mmol) was added to a stirring solution of 2-(chloromethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline (3.0 g, 9.50 mmol) in dichloromethane (60 mL). After 15.5 hours, ammonium hydroxide (12 mL) and then p-toluenesulfonyl chloride (2.2 g, 11.4 mmol) were added to the stirring solution and the biphasic mixture was stirred at ambient temperature for 3 hours. The reaction was diluted with water (50 mL) and then transferred to a separatory funnel. The aqueous layer was extracted with dichloromethane (3×100 mL) and the combined organic fractions dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using a HORIZON HPFC system (silica cartridge, eluting with 3-20% methanol in dichloromethane) to provide 1.6 g of 2-(chloromethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a yellow solid.

후처리

  1. customtransferred to a separatory funnel
  2. extractionThe aqueous layer was extracted with dichloromethane (3×100 mL)
  3. dry with materialthe combined organic fractions dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography
  7. washa HORIZON HPFC system (silica cartridge, eluting with 3-20% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-678f37f3eea74cd8ae0bc1ee35ae8284
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178677B2

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