Citric Acid → Diethyl butyl[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]malonate

HRID 64492

反応式

HRID 64492 の反応式
[CH2:1]([O:3][C:4](=[O:34])[CH:5]([NH:11][C:12]([C:14]1[N:18]2[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH2:24][C:25]3[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=3[F:32])[C:17]2=[N:16][C:15]=1[CH3:33])=[O:13])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[O-]CC.[Na+].C(O)C.I[CH2:43][CH2:44][CH2:45][CH3:46].[O-]CC.[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)C>[CH2:43]([C:5]([NH:11][C:12]([C:14]1[N:18]2[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH2:24][C:25]3[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=3[F:32])[C:17]2=[N:16][C:15]=1[CH3:33])=[O:13])([C:4]([O:3][CH2:1][CH3:2])=[O:34])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:44][CH2:45][CH3:46]

参加物

9

反応物 6

HCID 311Citric AcidHCID 10962Butyl iodideHCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 23706232Ethanol sodium ethoxideHCID 86713528Diethyl[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]malonate

生成物 1

HCID 86713527Diethyl butyl[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]malonate

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6212Chloroform溶媒

反応条件

温度
70 °C

実験手順

To 252 mg of diethyl[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]malonate were added 4 ml of ethanol, 0.23 ml of a 20% sodium ethoxide/ethanol solution, and 0.31 ml of 1-iodobutane, followed by stirring at 70° C. for 3 hours. Subsequently, 11 mg of sodium ethoxide was added thereto, followed by stirring at 70° C. for 1 hour. To the reaction mixture were added an aqueous citric acid solution, a saturated aqueous sodium hydrogen carbonate solution, and chloroform to carry out a layer separation operation. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 69 mg of diethyl butyl[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]malonate.

後処理

  1. stirringby stirring at 70° C. for 1 hour
  2. customa layer separation operation
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-af7d2113700a453d8a8cb158194c14ec
出典データセット
uspto-grants-2016_09
特許番号
US09447090B2

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