Dimethylformamide → N-(2-{4-amino-2-(ethoxymethyl)-7-[(3-thien-2-ylprop-2-ynyl)oxy]-1H-imidazo[4,5-c]quinolin-1-yl}-1,1-dimethylethyl)methanesulfonamide

HRID 2383225노트

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HRID 2383225 반응식
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:24][O:25][CH2:26][CH3:27])[N:14]([CH2:15][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:28][CH2:29][C:30]#[CH:31])=[CH:5][C:4]=2[N:3]=1.I[C:33]1[S:34][CH:35]=[CH:36][CH:37]=1.C(N(CC)CC)C.CN(C=O)C>ClCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.CO.O>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:24][O:25][CH2:26][CH3:27])[N:14]([CH2:15][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])([CH3:17])[CH3:18])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:28][CH2:29][C:30]#[C:31][C:33]3[S:34][CH:35]=[CH:36][CH:37]=3)=[CH:5][C:4]=2[N:3]=1

참가 물질

10

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 189212-IodothiopheneHCID 86626178N-{2-[4-amino-2-(ethoxymethyl)-7-(prop-2-ynyloxy)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide

생성물 1

HCID 67051119N-(2-{4-amino-2-(ethoxymethyl)-7-[(3-thien-2-ylprop-2-ynyl)oxy]-1H-imidazo[4,5-c]quinolin-1-yl}-1,1-dimethylethyl)methanesulfonamide수율 127.3%

시약·촉매·용매 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매

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온도
60 °C

실험 절차

N-{2-[4-Amino-2-(ethoxymethyl)-7-(prop-2-ynyloxy)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide (600 mg, 1.34 mmol), 2-iodothiophene (565 mg, 2.69 mmol), triethylamine (0.50 mL, 3.5 mmol), dichlorobis(triphenylphosphine)palladium(II) (19 mg, 0.03 mmol), copper(I) iodide (10 mg, 0.05 mmol), and DMF (10 mL) were combined and heated at 60° C. overnight. After cooling to ambient temperature, the reaction was poured into water (200 mL) and a fine precipitate formed. After the mixture was stirred for 1 hour, the solid was isolated by filtration. The solid was dissolved in dichloromethane and methanol and was passed through a plug of silica gel, which was rinsed with 20% methanol in dichloromethane. The filtrate was concentrated under reduced pressure to yield approximately 900 mg of N-(2-{4-amino-2-(ethoxymethyl)-7-[(3-thien-2-ylprop-2-ynyl)oxy]-1H-imidazo[4,5-c]quinolin-1-yl}-1,1-dimethylethyl)methanesulfonamide as a dark brown semi-solid that was used without further purification in the next step.

후처리

  1. temperatureAfter cooling to ambient temperature
  2. customa fine precipitate formed
  3. customthe solid was isolated by filtration
  4. washwas rinsed with 20% methanol in dichloromethane
  5. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-a7b6ec6fd7994f1c823a25c4e6fa8af0
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263594B2

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