Propanal → N-(8-(2,4-dichlorophenyl)-2-ethylimidazo[1,2-a]pyrazin-3-yl]-N,N-dipropylamine

HRID 501014노트

반응식

HRID 501014 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([C:15]([NH:20][CH2:21][CH2:22][CH3:23])=[C:16]([CH2:18][CH3:19])[N:17]=2)[CH:12]=[CH:13][N:14]=1.[CH:24](=O)[CH2:25][CH3:26].S(=O)(=O)(O)O.[BH4-].[Na+].[OH-].[Na+]>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([C:15]([N:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])=[C:16]([CH2:18][CH3:19])[N:17]=2)[CH:12]=[CH:13][N:14]=1

참가 물질

8

반응물 5

HCID 527PropanalHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 22024528HCID 22024528, 화합물

생성물 1

HCID 22024404N-(8-(2,4-dichlorophenyl)-2-ethylimidazo[1,2-a]pyrazin-3-yl]-N,N-dipropylamine수율 81.8%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

N-[8-(2,4-Dichlorophenyl)-2-ethylimidazo[1,2-a]pyrazin-3-yl]-N-propylamine (296 mg, 0.85 mmol) and propionaldehyde (0.19 mL, 2.6 mmol) were dissolved in tetrahydrofuran (1.1 mL), and 3M sulfuric acid (0.87 mL, 2.6 mmol) was added thereto. Sodium borohydride (70 mg) was added thereto under ice-cooling, and the mixture was stirred for 3 hours. Water was added to the reaction mixture, which was neutralized with a 2N aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:2) to give N-[8-(2,4-dichlorophenyl)-2-ethylimidazo[1,2-a]pyrazin-3-yl]-N,N-dipropylamine (272 mg) as pale yellow crystals. The resulting free compound was converted into hydrochloride with hydrochloric acid-ether using the conventional method, to give the title compound (250 mg) as white crystals.

후처리

  1. temperatureunder ice-cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:2)

출처 및 근거

ORD 기록
ord-9e64cf8c04e640b892b9ce8cdc4340d3
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772249B2

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