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

HRID 1762218ノート

反応式

HRID 1762218 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9a4c090ae90c441f97e9abc2102bed77
出典データセット
uspto-grants-1989_05
特許番号
US04831041

反応ノート

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