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

HRID 432705ノート

反応式

HRID 432705 の反応式
[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

参加物

7

反応物 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)

生成物 1

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

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒HCID 72391,2-Dichlorobenzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4ff2774b26e248109b42a10e3a53d1f0
出典データセット
uspto-grants-2003_12
特許番号
US06664260B2

反応ノート

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