Ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropanoate → Ethyl 2-[6-[5-[4-(Diphenylmethoxy)piperidino]pentylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate Difumarate

HRID 1169057ノート

反応式

HRID 1169057 の反応式
[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:28]1[CH:29]=[CH:30][C:31]2[N:32]([CH:34]=[C:35]([C:37]([CH3:44])([CH3:43])[C:38]([O:40][CH2:41][CH3:42])=[O:39])[N:36]=2)[N:33]=1.O1CCCC1.[C:50]([O:53]CC)(=[O:52])[CH3:51]>>[C:38]([OH:40])(=[O:39])/[CH:37]=[CH:51]/[C:50]([OH:53])=[O:52].[C:38]([OH:40])(=[O:39])/[CH:37]=[CH:51]/[C:50]([OH:53])=[O:52].[C:1]1([CH:7]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:28]3[CH:29]=[CH:30][C:31]4[N:32]([CH:34]=[C:35]([C:37]([CH3:43])([CH3:44])[C:38]([O:40][CH2:41][CH3:42])=[O:39])[N:36]=4)[N:33]=3)[CH2:11][CH2:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

4

反応物 3

HCID 11043751Ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropanoateHCID 21939870Tetrahydrofuran ethyl acetateHCID 229893744-(Diphenylmethoxy)-1-piperidinepentanamine

生成物 1

HCID 69842837Ethyl 2-[6-[5-[4-(Diphenylmethoxy)piperidino]pentylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate Difumarate

実験手順

1.41 g of 4-(diphenylmethoxy)-1-piperidinepentanamine and 0.536 g of ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropionate were stirred at 190-200° C. for 3.5 hours. After cooling, ethyl acetate tetrahydrofuran (2:1) was added; the mixture was washed with aqueous sodium bicarbonate and saturated saline, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate:methanol:triethylamine (185:15:2). The desired fraction was collected, dissolved in 5 ml of ethanol; a solution of 235 mg of fumaric acid in 5 ml of methanol was added, followed by concentration. Ethyl ether was added to the residue; the resulting powder was collected by filtration, washed with ethyl ether and dried to yield 0.629 g of the title compound.

後処理

  1. temperatureAfter cooling
  2. washthe mixture was washed with aqueous sodium bicarbonate and saturated saline
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluted with ethyl acetate:methanol:triethylamine (185:15:2)
  6. customThe desired fraction was collected
  7. dissolutiondissolved in 5 ml of ethanol
  8. additiona solution of 235 mg of fumaric acid in 5 ml of methanol was added
  9. concentrationfollowed by concentration
  10. additionEthyl ether was added to the residue
  11. filtrationthe resulting powder was collected by filtration
  12. washwashed with ethyl ether
  13. customdried

出典と根拠

ORDレコード
ord-f27fe4dec29640a68295baa9919fa523
出典データセット
uspto-grants-2003_09
特許番号
US06627630B1

反応ノート

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