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Lithium Hydroxide → (S)-3-(4-Amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)-5-hydroxybenzoic acid

HRID 1052668
ノート
印刷プレビュー

反応式

HRID 1052668 の反応式
[NH2:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([OH:18])[CH:17]=2)[C:11]([O:13]C)=[O:12])=[C:6]([NH:19][C@H:20]([C:22]2[N:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:26](=[O:34])[C:25]3=[C:35]([CH3:38])[CH:36]=[CH:37][N:24]3[N:23]=2)[CH3:21])[N:5]=[CH:4][N:3]=1.[OH-].[Li+]>O1CCCC1.O>[NH2:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([OH:18])[CH:17]=2)[C:11]([OH:13])=[O:12])=[C:6]([NH:19][C@H:20]([C:22]2[N:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:26](=[O:34])[C:25]3=[C:35]([CH3:38])[CH:36]=[CH:37][N:24]3[N:23]=2)[CH3:21])[N:5]=[CH:4][N:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 131736113(S)-Methyl 3-(4-amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)-5-hydroxybenzoate

生成物 1

HCID 73776790(S)-3-(4-Amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)-5-hydroxybenzoic acid収率 72%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

(S)-Methyl 3-(4-amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)-5-hydroxybenzoate (35 mg, 0.07 mmol) was dissolved in 5 mL tetrahydrofuran. Lithium hydroxide in 5 mL water was added and the mixture was stirred at 50° C. for 4 h. The solvent was evaporated and the residue was re-dissolved in dichloromethane. The aqueous phase was acidified with 2N hydrochloric acid. The aqueous was further extracted with dichloromethane and was washed with water and brine, dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified by reverse phase using SP1 ® Purification System to obtain 25 mg (72% yield) of the title compound as a white solid. Purity 97%.

後処理

  1. customThe solvent was evaporated
  2. dissolutionthe residue was re-dissolved in dichloromethane
  3. extractionThe aqueous was further extracted with dichloromethane
  4. washwas washed with water and brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by reverse phase
  9. custom® Purification System

出典と根拠

ORDレコード
ord-9357ae05949f4d57a44df4b6d5edf399
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09388189B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート