Sodium Bicarbonate → HCID 71269976、化合物

HRID 518255

反応式

HRID 518255 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[N:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:13](=[O:22])[C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[CH3:10])[C:5](C#N)=[CH:4][N:3]=1.[C:31]([O-:34])(O)=[O:32].[Na+]>O1CCOCC1.S(=O)(=O)(O)O.O>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[N:12]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:13](=[O:22])[C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[CH3:10])[C:5]([C:31]([OH:34])=[O:32])=[CH:4][N:3]=1

参加物

5

反応物 2

HCID 516892Sodium BicarbonateHCID 67950671(S)-2-amino-4-((1-(8-chloro-1-oxo-2-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl)amino)pyrimidine-5-carbonitrile

生成物 1

HCID 71269976HCID 71269976、化合物

試薬・触媒・溶媒 2

HCID 312751,4-Dioxane溶媒HCID 21910475Sulfuric acid hydrate (1:1)溶媒

反応条件

温度
90 °C

実験手順

To a solution of (S)-2-amino-4-((1-(8-chloro-1-oxo-2-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl)amino)pyrimidine-5-carbonitrile (53) (495 mg, 1.19 mmol) in anhydrous 1,4-dioxane (20 mL), sulfuric acid/water (1:1, 7 mL) was added dropwise. The reaction mixture was stirred at 90° C. for 60 h. The mixture was allowed to cool to RT and basified with NaHCO3. The precipitate was collected by filtration and then dissolved in water. The resulting mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to afford the product 117, (S)-2-amino-4-((1-(8-chloro-1-oxo-2-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl)amino)pyrimidine-5-carboxylic acid. The material was used directly in the next step.

後処理

  1. filtrationThe precipitate was collected by filtration
  2. dissolutiondissolved in water
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-fc2485470f2a4bb096c0cc8e6f2c4b57
出典データセット
uspto-grants-2015_08
特許番号
US09115141B2

関連ノート

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