Triethyl phosphonoacetate → ethyl (4-{6-[(2'-cyanobiphenyl-4-yl)methyl]-5-oxo-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-4(5H)-yl}cyclohexylidene)acetate

HRID 519574ノート

反応式

HRID 519574 の反応式
[CH2:1]([O:3][C:4](=[O:14])[CH2:5]P(OCC)(OCC)=O)[CH3:2].[H-].[Na+].[O:17]=[C:18]1[C:23]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[C:32]([C:37]#[N:38])=[CH:33][CH:34]=[CH:35][CH:36]=3)=[CH:27][CH:26]=2)=[C:22]([CH2:39][CH2:40][CH3:41])[N:21]2[N:42]=[CH:43][N:44]=[C:20]2[N:19]1[CH:45]1[CH2:50][CH2:49][C:48](=O)[CH2:47][CH2:46]1>O1CCCC1>[C:37]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[C:28]1[CH:27]=[CH:26][C:25]([CH2:24][C:23]2[C:18](=[O:17])[N:19]([CH:45]3[CH2:50][CH2:49][C:48](=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[O:14])[CH2:47][CH2:46]3)[C:20]3[N:21]([N:42]=[CH:43][N:44]=3)[C:22]=2[CH2:39][CH2:40][CH3:41])=[CH:30][CH:29]=1)#[N:38]

参加物

5

反応物 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 670088534'-{[5-Oxo-4-(4-oxocyclohexyl)-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile

生成物 1

HCID 86644029ethyl (4-{6-[(2'-cyanobiphenyl-4-yl)methyl]-5-oxo-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-4(5H)-yl}cyclohexylidene)acetate収率 86%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution (10 mL) of ethyl(diethoxyphosphoryl)acetate (1.2 g) in tetrahydrofuran was added sodium hydride (0.21 g), and the mixture was stirred at room temperature for 1 hr. A solution (10 mL) of 4′-{[5-oxo-4-(4-oxocyclohexyl)-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (2 g) in tetrahydrofuran was added to the reaction mixture, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was extracted with 1 N hydrochloric acid and ethyl acetate, and the obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (1.9 g, 86%).

後処理

  1. stirringthe mixture was stirred at room temperature for 3 hr
  2. extractionThe reaction mixture was extracted with 1 N hydrochloric acid and ethyl acetate
  3. washthe obtained ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-960b25b1af4e49549c00b1589a190e76
出典データセット
uspto-grants-2015_08
特許番号
US09115136B2

反応ノート

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