Trifluoroacetic acid → HCID 12114211, 화합물

HRID 967050

반응식

HRID 967050 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].C(=O)([O-])[O-].[K+].[K+].I[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.FC(F)(F)C(O)=O>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.C(#N)C.O.CN(C)C=O>[C:28]1([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:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

9

반응물 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 98566101-[2-(2-propynyloxy)ethyl)-1H-imidazo[4,5-c]quinolin-4-amine

생성물 1

HCID 12114211HCID 12114211, 화합물수율 21%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 18373917Acetonitrile--water (1/1)용매

반응 조건

온도
70 °C

실험 절차

Under a nitrogen atmosphere, a mixture of 1-[2-(2-propynyloxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine (10 g, 37.6 mmol), anhydrous N,N-dimethylformamide (150 mL) and potassium carbonate (6.23 g, 45.1 mmol) was heated to 70° C. Iodobenzene (4.43 mL, 39.5 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.53 g, 0.75 mol), and copper(I) iodide (0.29 g, 1.50 mmol) were added and the mixture was allowed to stir for 0.5 hour. The temperature was raised to about 85° C. After 1.5 hours analysis by HPLC (reverse phase, acetonitrile/water with 0.1% trifluoroacetic acid) indicated that the reaction was complete. The mixture was allowed to cool to ambient temperature and then it was filtered. The filtrate was concentrated under reduced pressure. The residue was purified twice by flash chromatography (95/5 dichloromethane/methanol) to provide 2.7 g of 1-{2-[(3-phenyl-2-propynyl)oxy]ethyl}-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, m.p. 196-197° C.

후처리

  1. temperatureThe temperature was raised to about 85° C
  2. temperatureto cool to ambient temperature
  3. filtrationit was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified twice by flash chromatography (95/5 dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-85bcc2f639e241319376e689818f45d5
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06953804B2

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