Triphenylphosphine → 2-methyl-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinoline-4-amine

HRID 432705노트

반응식

HRID 432705 반응식
[CH3:1][C:2]1[N:3]([CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]3N=N[N:16]=[C:6]3[C:5]=2[N:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+].O>ClC1C=CC=CC=1Cl.ClCCl.CCOCC>[CH3:1][C:2]1[N:3]([CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([NH2:16])[C:5]=2[N:17]=1

참가 물질

7

반응물 3

HCID 11776TriphenylphosphineHCID 187601655-methyl-6-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinolineHCID 23719242Sodium hydroxide--water (1/1/1)

생성물 1

HCID 97990342-methyl-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinoline-4-amine수율 23.4%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매HCID 72391,2-Dichlorobenzene용매

실험 절차

Under an atmosphere of nitrogen, 5-methyl-6-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline (0.73 g, 1.89 mmol) and triphenylphosphine (0.64 g, 2.84 mmol) were dissolved in 1,2-dichlorobenzene (15 ml). The reaction was heated at reflux for 18 hours. After cooling to ambient temperature, the solvent was removed in vacuo. The resulting residue was treated with 1N HCl/water (30 ml) and vigorous stirring produced an off white suspension. The solid was removed by filtration leaving a yellow filtrate. The filtrate was treated with 10% sodium hydroxide/water until pH 11 was reached. The filtrate was extracted with dichloromethane (3×25 ml). The combined organic fractions were washed with brine (25 ml), dried (Na2SO4), filtered and concentrated in vaeuo to yield an orange oil. The oil was dissolved in a minimum amount of dichloromethane and diluted with ether to produce a precipitate. The solid was recrystallized from n-propyl acetate to yield 0.16 g of 2-methyl-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinoline-4-amine as a tan solid, m.p. 145.0-146.0.

후처리

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 hours
  3. customthe solvent was removed in vacuo
  4. additionThe resulting residue was treated with 1N HCl/water (30 ml)
  5. customproduced an off white suspension
  6. customThe solid was removed by filtration
  7. customleaving a yellow filtrate
  8. extractionThe filtrate was extracted with dichloromethane (3×25 ml)
  9. washThe combined organic fractions were washed with brine (25 ml)
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vaeuo
  13. customto yield an orange oil
  14. customto produce a precipitate
  15. customThe solid was recrystallized from n-propyl acetate

출처 및 근거

ORD 기록
ord-4ff2774b26e248109b42a10e3a53d1f0
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664260B2

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