Dimethylamine → 8-(2-Methoxycarbonylamino-6-methylbenzyloxy)-2-methylimidazo-[1,2-a]pyridine

HRID 1762218노트

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HRID 1762218 반응식
[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:7]=1[CH2:8][O:9][C:10]1[C:11]2[N:12]([C:16](CC#C)=[C:17]([CH3:19])[N:18]=2)[CH:13]=[CH:14][CH:15]=1)=[O:4].C=O.CNC>O1CCOCC1.O>[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:7]=1[CH2:8][O:9][C:10]1[C:11]2[N:12]([CH:16]=[C:17]([CH3:19])[N:18]=2)[CH:13]=[CH:14][CH:15]=1)=[O:4]

참가 물질

6

반응물 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 1952178-(2-Methoxycarbonylamino-6-methylbenzyloxy)-2-methyl-3-(2-propynyl)imidazo(1,2-a)pyridine

생성물 1

HCID 538915038-(2-Methoxycarbonylamino-6-methylbenzyloxy)-2-methylimidazo-[1,2-a]pyridine수율 85%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
50 °C

실험 절차

To a solution of 8-(2-methoxycarbonylamino-6-methylbenzyloxy)-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridine (230 mg) in 1.4-dioxane (4.6 ml) were added 36% formaldehyde (105 mg), 50% dimethylamine in water (142 mg) and cuprous chloride (12.5 mg). After the mixture was stirred at 50° C. for 5 hours, 1.4-dioxane was evaporated under reduced pressure. The resultant residue was dissolved in chloroform (20 ml) and insoluble material was filtered off. The filtrate was washed with an aqueous solution of sodium bicarbonate and water in turn, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was recrystallized from a mixture of ethyl acetate and n-hexane to give 3-(4-N,N-dimethylamino-2-butynyl(-8-(2-methoxycarbonylamino-6-methylbenzyloxy)-2-methylimidazo-[1,2-a]pyridine (175 mg).

후처리

  1. custom1.4-dioxane was evaporated under reduced pressure
  2. dissolutionThe resultant residue was dissolved in chloroform (20 ml)
  3. filtrationinsoluble material was filtered off
  4. washThe filtrate was washed with an aqueous solution of sodium bicarbonate and water in turn
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was recrystallized from a mixture of ethyl acetate and n-hexane

출처 및 근거

ORD 기록
ord-9a4c090ae90c441f97e9abc2102bed77
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04831041

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