2,6,7-trimethyl-1-{2-[(3-phenylprop-2-ynyl)oxy]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine → 2,6,7-trimethyl-1-[2-(3-phenylpropoxy)ethyl]-1H-imidazo[4,5-c]pyridin-4-amine

HRID 1245899ノート

反応式

HRID 1245899 の反応式
[CH3:1][C:2]1[N:3]([CH2:14][CH2:15][O:16][CH2:17][C:18]#[C:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:4]2[C:9]([CH3:10])=[C:8]([CH3:11])[N:7]=[C:6]([NH2:12])[C:5]=2[N:13]=1>[Pd].CO>[CH3:1][C:2]1[N:3]([CH2:14][CH2:15][O:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:4]2[C:9]([CH3:10])=[C:8]([CH3:11])[N:7]=[C:6]([NH2:12])[C:5]=2[N:13]=1

参加物

4

反応物 1

HCID 104720722,6,7-trimethyl-1-{2-[(3-phenylprop-2-ynyl)oxy]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine

生成物 1

HCID 219128802,6,7-trimethyl-1-[2-(3-phenylpropoxy)ethyl]-1H-imidazo[4,5-c]pyridin-4-amine収率 57.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

2,6,7-Trimethyl-1-{2-[(3-phenylprop-2-ynyl)oxy]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine (0.55 g, 1.645 mmol) from Part I of Example 7 was combined with 10% palladium on carbon (0.10 g) in a Parr reactor. Methanol (30 mL) was added to the resulting mixture under a nitrogen purge, and then the mixture was placed under hydrogen at a pressure of 310 kPa for 4 hours. The resulting reaction mixture was filtered through a layer of Celite™ filter agent, and the filtrate was concentrated under reduced pressure to a clear oil. The oil was dissolved in 5% methanol in diethyl ether (˜50 mL), and 1M hydrochloric acid in diethyl ether (1.7 mL) was added to the resulting solution. Volatiles were removed under reduced pressure, and the resulting solids were dissolved in water. The aqueous solution was stirred for 10 minutes when the product oiled out of solution. The aqueous portion was washed with dichloromethane (3×). The combined organic portions were washed with water (2×) and brine (3×), dried with magnesium sulfate, filtered, and concentrated to a glassy oil under reduced pressure. The oil was triturated with diethyl ether. The solids that formed after 10 minutes of stirring were filtered off and dried for 18 hours to provide 0.3185 g of 2,6,7-trimethyl-1-[2-(3-phenylpropoxy)ethyl]-1H-imidazo[4,5-c]pyridin-4-amine, m.p. 118.1–119.0° C.

後処理

  1. custompurge
  2. customThe resulting reaction mixture
  3. filtrationwas filtered through a layer of Celite™
  4. filtrationfilter agent
  5. concentrationthe filtrate was concentrated under reduced pressure to a clear oil
  6. dissolutionThe oil was dissolved in 5% methanol in diethyl ether (˜50 mL)
  7. addition1M hydrochloric acid in diethyl ether (1.7 mL) was added to the resulting solution
  8. customVolatiles were removed under reduced pressure
  9. dissolutionthe resulting solids were dissolved in water
  10. washThe aqueous portion was washed with dichloromethane (3×)
  11. washThe combined organic portions were washed with water (2×) and brine (3×)
  12. dry with materialdried with magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated to a glassy oil under reduced pressure
  15. customThe oil was triturated with diethyl ether
  16. customThe solids that formed after 10 minutes
  17. stirringof stirring
  18. filtrationwere filtered off
  19. customdried for 18 hours

出典と根拠

ORDレコード
ord-161c3f0881a940588f6c43d692d965c1
出典データセット
uspto-grants-2006_10
特許番号
US07125890B2

反応ノート

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