Dimethylformamide → HCID 12114211, 화합물

HRID 433970

반응식

HRID 433970 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].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].F[C:33](F)(F)[C:34](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>[C:34]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:18][CH:19]=[CH:10][CH:11]=1

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 98566101-[2-(2-propynyloxy)ethyl)-1H-imidazo[4,5-c]quinolin-4-amine

생성물 1

HCID 12114211HCID 12114211, 화합물

시약·촉매·용매 3

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

반응 조건

온도
85 °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. lodobenzene (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. additionwere added
  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-d5a4024a39d344898ec0b79911be0166
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06670372B2

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