Ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropanoate → Ethyl 2-[6-[3-[4-(Diphenylmethoxy)piperidino]-2-hydroxypropylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate Difumarate

HRID 1169058노트

반응식

HRID 1169058 반응식
[NH2:1][CH2:2][CH:3]([OH:25])[CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([O:11][CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][CH2:6]1.Cl[C:27]1[CH:28]=[CH:29][C:30]2[N:31]([CH:33]=[C:34]([C:36]([CH3:43])([CH3:42])[C:37]([O:39][CH2:40][CH3:41])=[O:38])[N:35]=2)[N:32]=1.[C:44]([O:47]CC)(=[O:46])[CH3:45].O1CCCC1>>[C:37]([OH:39])(=[O:38])/[CH:36]=[CH:45]/[C:44]([OH:47])=[O:46].[C:37]([OH:39])(=[O:38])/[CH:36]=[CH:45]/[C:44]([OH:47])=[O:46].[C:13]1([CH:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:11][CH:8]2[CH2:9][CH2:10][N:5]([CH2:4][CH:3]([OH:25])[CH2:2][NH:1][C:27]3[CH:28]=[CH:29][C:30]4[N:31]([CH:33]=[C:34]([C:36]([CH3:42])([CH3:43])[C:37]([O:39][CH2:40][CH3:41])=[O:38])[N:35]=4)[N:32]=3)[CH2:6][CH2:7]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

4

반응물 3

HCID 11043751Ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropanoateHCID 21939870Tetrahydrofuran ethyl acetateHCID 229892803-[4-(Diphenylmethoxy)piperidino]-2-hydroxypropylamine

생성물 1

HCID 69842735Ethyl 2-[6-[3-[4-(Diphenylmethoxy)piperidino]-2-hydroxypropylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate Difumarate

실험 절차

0.511 g of 1-amino-3-[4-(diphenylmethoxy)piperidino]-2-propanol and 0.268 g of ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropionate were stirred at 190-200° C. for 3 hours. After cooling, ethyl acetate-tetrahydrofuran (2:1) was added; the mixture was washed with aqueous sodium bicarbonate and saturated saline, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate:methanol:triethylamine (90:10:1). The desired fraction was collected, dissolved in 5 ml of ethyl acetate; a solution of 82 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 0.223 g of the title compound.

후처리

  1. temperatureAfter cooling
  2. washthe mixture was washed with aqueous sodium bicarbonate and saturated saline
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluted with ethyl acetate:methanol:triethylamine (90:10:1)
  6. customThe desired fraction was collected
  7. dissolutiondissolved in 5 ml of ethyl acetate
  8. additiona solution of 82 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

출처 및 근거

ORD 기록
ord-d9101745a8c547a99908d301cd497147
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06627630B1

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