Methanol → 1-(2-{[3-(3,4-dimethylphenyl)-2-propynyl]oxy}ethyl]-1H-imidazo[4,5-c]quinolin-4-amine

HRID 433980

반응식

HRID 433980 반응식
[CH2:1]([O:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[CH:8]1)[C:2]#[CH:3].I[C:22]1[CH:23]=[C:24]([CH3:29])[C:25]([CH3:28])=[CH:26][CH:27]=1.N1CCCC1.CO>C(Cl)(Cl)Cl.[Cu]I.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>[CH3:29][C:24]1[CH:23]=[C:22]([C:3]#[C:2][CH2:1][O:4][CH2:5][CH2:6][N:7]2[C:19]3[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[N:12]=[C:11]([NH2:20])[C:10]=3[N:9]=[CH:8]2)[CH:27]=[CH:26][C:25]=1[CH3:28]

참가 물질

8

반응물 4

HCID 887MethanolHCID 31268PyrrolidineHCID 1416464-Iodo-1,2-dimethylbenzeneHCID 98566101-[2-(2-propynyloxy)ethyl)-1H-imidazo[4,5-c]quinolin-4-amine

생성물 1

HCID 222544631-(2-{[3-(3,4-dimethylphenyl)-2-propynyl]oxy}ethyl]-1H-imidazo[4,5-c]quinolin-4-amine수율 14.2%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6212Chloroform용매

실험 절차

Under a nitrogen atmosphere, 1-[2-(2-propynyloxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine (0.5 g, 1.9 mmol), copper (I) iodide (0.036 g, 0.2 mmol), 4-iodo-orthoxylene (0.5 g, 2.1 mmol) and pyrrolidine (10 mL) were combined and stirred at ambient temperature. Dichlorobis(triphenylphosphine)palladium(II) (0.066 g, 0.1 mmol) was added and the reaction mixture was stirred at ambient temperature for 1 hour. Analysis by TLC (30% methanol in chloroform) indicated that starting material was still present. The reaction mixture was heated at 65° C. overnight. The pyrrolidine was removed under reduced pressure. The resulting residue was triturated with dichloromethane containing methanol. The insoluble material was isolated by filtration and then recrystallized from toluene (40 mL) to provide 0.1 g of 1-(2-{[3-(3,4-dimethylphenyl)-2-propynyl]oxy}ethyl]-1H-imidazo[4,5-c]quinolin-4-amine as a solid, m.p. 214-216° C. Analysis: Calculated for C23H22N4O: %C, 74.57; %H, 5.99; %N, 15.12; Found: %C, 74.24; %H, 5.98; %N, 15.08. 1H-NMR (300 MHz; DMSO-d6) δ (ppm) 8.167(s, 1H), 8.112(d, J=7.3 Hz, 1H), 7.628(d, J=8.3 Hz, 1H), 7.44(t, J=7.3 Hz, 1H), 7.232(t, J=6.8 Hz, 1H), 7.078(d, J=7.8 Hz, 1H), 7.024(s, 1H), 6.952(d, J=7.9 Hz, 1H), 6.586(s, 2H), 4.849(t, J=5 Hz, 2H), 4.365(s, 2H), 4.015(t, J=5.6 Hz, 2H), 2.197(s, 3H), 2.159(s, 3H).

후처리

  1. stirringthe reaction mixture was stirred at ambient temperature for 1 hour
  2. temperatureThe reaction mixture was heated at 65° C. overnight
  3. customThe pyrrolidine was removed under reduced pressure
  4. customThe resulting residue was triturated with dichloromethane
  5. additioncontaining methanol
  6. customThe insoluble material was isolated by filtration
  7. customrecrystallized from toluene (40 mL)

출처 및 근거

ORD 기록
ord-3c8cb814284242108e2b7ba991942776
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06670372B2

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